Name: 613-92-3|N'-Hydroxybenzimidamide|98%
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1
[ 108-30-5 ]
[ 613-92-3 ]
[ 24088-59-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	In 1,4-dioxane at 200℃; for 0.166667h;	48.a Example 48; 4-[3-(3-Phenyl-l,2,4-oxadiazol-5-yl)propanoyl]aminothiophene-3-carboxylic Add; a) 3-(3-Phenyl-l,2,4-oxadiazol-5-yl)propanoic Acid; To N'-hydroxybenzenecarboximidamide (1.00 g, 7.34 mmol) in 1,4-dioxane (4 mL, EPO 50 mmol) was added succinic anhydride (735 mg, 7.34 mmol). The reaction was heated to 200 °C for 600 s. After cooling to room temperature, the reaction mixture was purified via Combi-flash. to give the desired product (1.4 g, 87%).
68%	Stage #1: N-hydroxybenzenecarboximidamide With sodium hydroxide In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: succinic acid anhydride In dimethyl sulfoxide at 20℃; for 3h;	General procedure for the synthesis of 1,2,4-oxadiazoles 4a-u from amidoximes 1 and cyclicanhydrides 2 in DMSO. Method B. General procedure: To a solution of amidoxime 1 (2.5 mmol) in DMSO (2-3 mL) was rapidly added powdered NaOH (5 mmol). The reaction mixture was stirred at room temperature for 20 min, then to the mixture was added a cyclic anhydride 2 (2.5 mmol). The reaction mixture was stirred at room temperature for a 3 h. The reaction mixture was diluted with cold water (30 mL) followed by the addition of hydrochloric acid to pH ~1. The resulting precipitate was filtered off, washed with cold water (25 mL) and dried in air at 50 °C.
	microwave irradiation;

In neat (no solvent) at 140℃; for 1h;

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2007/15744, 2007, A1 Location in patent: Page/Page column 63-64
[2]Tarasenko, Marina; Duderin, Nikolay; Sharonova, Tatyana; Baykov, Sergey; Shetnev, Anton; Smirnov, Alexey V. [Tetrahedron Letters, 2017, vol. 58, # 37, p. 3672 - 3677]
[3]Schulz [Chemische Berichte, 1885, vol. 18, p. 2459]
[4]Neves Filho, Ricardo A. W.; Srivastava, Rajendra M. [Molecules, 2006, vol. 11, # 5, p. 318 - 324]
[5]Barbosa, Andrey da S.; Barbosa, Andrey da S.; Maciel, Larissa G.; Soares, Thereza A.; de Alencar-Filho, Edilson B.; dos Anjos, Janaína V.

2
[ 541-41-3 ]
[ 613-92-3 ]
[ 1456-22-0 ]

Reference： [1]Chemische Berichte,1885,vol. 18,p. 2471
Chemische Berichte,1886,vol. 19,p. 1481

3
[ 100-47-0 ]
[ 613-92-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydroxylamine; In ethanol; water; for 48h;Heating / reflux;	Benzonitrile (0.99 cm3, 1 g, 9.7 mmol) and hydroxylamine (50% in water, 0.89 cm3, 0.96 g, 14.55 mmol, 1.5 eq) were stirred under reflux in EtOH (10 cm3) for 48 hours. The solvent was evaporated under reduced pressure and water (10 cm3) was added to the residue. The mixture was extracted with dichloromethane (100 cm3) and the organic extract was evaporated under reduced pressure. The residue was purified by column chromatography to give the product N'-hydroxybenzimidamide (1.32 g, 100%) as a white crystalline solid, mp 79-81 C. (lit 79-80 C.
96.5%	With hydroxylamine hydrochloride; sodium hydroxide; In methanol; at 55 - 60℃; for 2h;	Hydroxylamine hydrochloride (8.85 g, 0.126 moles) and methanol (45 mL) were charged to a 100 mL flask, followed by 51% sodium hydroxide (9.82 g, 0.125 moles). To this mixture was added benzonitrile (10.32 g, 0.100 moles), and the reaction was heated to 55-60C and held for 2 hours. HPLC showed that the reaction was complete by the disappearance of benzonitrile. A portion of the methanol (30 mL) was removed by distillation, deionized (DI) water was added (22 mL), and the remaining methanol was distilled at 300 torr to give two liquid phases (benzamide oxime melt and salt water). 2-Methyltetrahydrofuran (20.0 g) was added, and the aqueous salt phase was drained off to give 33.34 g of a solution of benzamide oxime in 2-methyltetrahydrofuran, 39.45% by loss on drying and HPLC. The yield of benzamide oxime was 96.5%.
95%	With hydroxylamine hydrochloride; triethylamine; In methanol; at 60℃; for 0.5h;	Weigh benzonitrile (2g, 19.39mmol), hydroxylamine hydrochloride (2.7g, 38.79mmol) and triethylamine (3.93g, 38.79mmol), add methanol (100ml), and heat to 60 C for 30min. The TLC test was complete. The methanol was distilled off under reduced pressure, and ethyl acetate (50 ml) was added to the reaction flask, followed by washing with saturated brine (30 ml × 4). The organic phase was dried over anhydrous MgSO4 overnight, filtered, and the ethyl acetate was distilled off under reduced pressure to obtain 2.5 g of a white solid product with a yield of 95%.

93%	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 20℃; for 72h;	Hydroxylammonium chloride (0.2mol) and sodium carbonate(0.1mol) were dissolved in water (50 mL) and addedto a solution of benzonitrile (0.1 mol) in 50 ml ethanol 96%and stirred for 72 h at room temperature. The reaction mixturewas extracted with diethyl ether and the organic layerwas dried with anhydrous sodium sulfate and evaporated togive the product.Yield: 93%, M.p. 72-73C, IR (KBr) ..max (cm-1): 3330-3050, 3305, 3243. For C7H8N2O calculated: C 61.75, H 5.92,N 20.58; found: C 61.78, H 5.90, N 20.54. MS [M+1]+: m/z137
90%	With hydroxylamine hydrochloride; triethylamine; In methanol; at 60℃; for 1h;	The benzonitrile (3.1 g, 30.0 mmol) is placed in the reaction bottle, adding methanol to 40 ml, adding hydroxylamine hydrochloride (4.2 g, 60.0 mmol), triethylamine (6.1 g, 60.0 mmol), heating to 60 C reaction 1 h, cooling to room temperature, evaporate the solvent under reduced pressure, the residue water and ethyl acetate to dissolve, separating the organic phase, the aqueous phase is extracted with ethyl acetate three times, the combined organic phase, dried with anhydrous sodium sulfate, filtered, reducing pressure and ethyl acetate shall benzamide oxime (s). Benzamide oxime: white solid; 3.68 g, yield 90.0%;
89%	With potassium phosphate; hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 90℃; for 0.75h;	General procedure: To a suspension of hydroxylamine hydrochloride (2.5 mmol) and K3PO4 (3 mmol) in DMF (4 mL), nitrile (2 mmol) was added. The reaction mixture was heated at 90 C for 30-60 min. After nearly complete conversion to the corresponding amidoxime, as was indicated by TLC monitoring, acid chloride (2 mmol) was added dropwise, and the mixture was heated at 110 C for further 20-60 min. On completion of the reaction (TLC), the hot mixture was poured into ice-water (50 mL). In the case of the products 7a, 7b-7f and 7h-7m the obtained crude solids were purified by recrystallization from 95% ethanol, and the oxadiazoles 7b and 7g were purified, after extraction with CHCl3 (2 × 10 mL) and drying (Na2SO4), by preparative TLC ( silica gel, cyclohexane-EtOAc, 1:3 as eluent).
89%	With hydroxylamine hydrochloride; triethylamine; In water; at 25℃; for 6h;Green chemistry;	General procedure: A mixture of aryl nitrile 1a-g (20 mmol), hydroxylamine hydrochloride (2.08 g, 30 mmol) and triethylamine (4.46 mL, 32 mmol) in 40 mL distilled water was stirred at room temperature (25 C) for 6 h. After completion of the reaction (monitored by TLC), the products of 2b-g were filtered, washed with distilled water, dried and used without further purification. But in the case of benzamidoxime 2a, it was extracted from the reaction mixture using ethyl acetate (3 * 30 mL), the organic layer was then dried over anhydrous MgSO4, filtered and evaporated by using a rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (6 :1) as eluent.
86.2%	With hydroxylamine hydrochloride; potassium carbonate; In water; at 20 - 50℃; for 4.5h;	Hydroxylamine hydrochloride (208.5 g, 3.0 mol, 1.2 eq), water (400 mL), PEG- 2000 (13.7 g, 0.06 mol, 0.05 eq), potassium carbonate (517.5 g, 3.75 mol, 1.5 eq) Necked flask and stirred at room temperature for 30 min. Benzonitrile (257.8 g, 2.5 mol, 1.0 eq) was slowly added thereto. After the addition, the temperature was raised to 50 C. and incubated for 4 h. The disappearance of the starting material was monitored by TLC (VPE / EA = 1). After the reaction was completed, the reaction mixture was cooled to 5 C and 2N diluted hydrochloric acid was added to adjust the pH to 6-7. The solid was precipitated, filtered, vacuum-dried at 50 C,293.4g of benzamidoxime was obtained in a yield of 86.2%. Its m.p. was found to be 78-80 C with a purity of 98.7%.
83%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In methanol; for 5h;Reflux;	To a solution of benzonitrile (80 mmol) in MeOH (100mL), H2NOH.HCl (1.5 eq.) and NaHCO3 (1.6 eq.) were added at room temperature. The resulting mixture was allowed to reflux for 5 h. The reaction was cooled to room temperature, the solvent was removed under reduced pressure and the resulting mixture was extracted with EtOAc and H2O. The organic phase was washed with brine solution and concentrated under vacuum, affording the amidoxime as a colorless oil in 83% yield. Then, bromoacetylbromide (1.35 eq.) was added dropwise to a solution of the amidoxime and K2CO3 (1.35 eq.) in CHCl3 (60mL). The reaction was stirred at room temperature for 3 h. The solvent was removed, the mixture was extracted with EtOAc and H2O and the organic phase was washed with a brine solution, dried with Na2SO4, filtrated and concentrated under reduced pressure. The resulting mixture was dissolved in toluene (50mL) and heated at 100 C for 2 h. The reaction was cooled and the solvent removed.The resulting mixture was purified by chromatography on silicagel (eluent: EtOAc/hexane) which afforded the desired product as white solid. 4.2.1. 5-(bromomethyl)-3-phenyl-1,2,4-oxadiazole 2 White solid; Yield: 74%; m.p.: 48-50 C; 1H NMR (CDCl3;500 MHz) delta ppm: 8.08 (2H; dd; 3J = 8.0 Hz; 4J = 1.5 Hz), 7.51-7.46(3H; m), 4.56(2H; s) [33].13C RMN (CDCl3; 125 MHz) delta ppm:174.7,169.0, 131.6, 129.0, 127.6, 126.3, 16.6.
79%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: To a stirred suspension of nitrile (30 mmol) and hydroxylaminehydrochloride (3.13 g, 45 mmol) in EtOH (50 mL) a NaHCO3 (3.78 g,45 mmol)was added. The reaction mixturewas stirred under refluxfor 6 h. After the reaction had completed, the reaction mixture wasconcentrated under reduced pressure, and the residue was dilutedwith cold water (80 mL). The resulting precipitate was filtered off,washed with cold water (20 mL) and dried in air at roomtemperature.4.2.3. N'-Hydroxypicolinimidamide (10a) [35]Yield 3.54 g (86%); White solid; m.p. 117-118 C. 1H NMR(400 MHz, DMSO) delta ppm 9.90 (s, 1H), 8.57 (d, J 4.8 Hz, 1H), 7.86 (d,J 7.9 Hz, 1H), 7.82 (t, J 8.1 Hz, 1H), 7.40 (t, J 6.6 Hz, 1H), 5.80(br.s, 2H).
78%	With hydroxylamine hydrochloride; triethylamine; In ethanol; at 75℃; for 12h;Inert atmosphere;	General procedure: Triethylamine (42 mL, 0.3 mol) was added to a solution of benzonitrile (21, 10.3 g, 0.1 mol), hydroxylamine hydrochloride (20.9 g, 0.3 mol) and ethanol (150 mL) and stirred for 12 h at 75 C. The reaction mixture was cooled to room temperature and evaporated to dryness, extracted with DCM (300 mL)/water (100 mL). The organic layer dried with MgSO4, filtered and evaporated to dryness yielding the desired product 22 as a primrose yellow liquid (10.6 g, yield 78%). 1H NMR (300 MHz, DMSO-d6): delta = 9.59 (s, 1H), 7.62-7.67 (m, 2H), 7.32-7.37 (m, 3H), 5.77 (s, 2H); LC/MS (ESI): m/z 137 [M + H]+.
77.58%	With hydroxylamine hydrochloride; potassium carbonate; In ethanol; for 34h;Reflux;	General procedure: The amidoximes were prepared as per procedure reported earlier in the literature [30]. Hydroxylamine hydrochloride (21.94 mmol, 1.518 g) and anhydrous potassium carbonate (43.8 mmol, 6.053 g) were added to ethanol (30 mL) at room temperature followed by the addition of acetonitrile/ appropriate aromatic nitrile (14.6 mmol). The mixture was refluxed till the completion of the reaction which was monitored by TLC. The solvent was evaporated and the residue was dissolved in EtOAc (50 mL). The organic layer was separated, washed twice with water and dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. The residue was left overnight at room temperature. The compound thus obtained was recrystallized using dichloromethane to give compounds 2a-f.
77%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).
77%	With hydroxylamine hydrochloride; potassium carbonate; In ethanol;Reflux;	A mixture of benzonitrile (2.0 g, 19.4 mmol), hydroxylamine hydrochloride (4.04 g , 58.2 mmol) and potassium carbonate (8.0 g, 58.2 mmole) in ethanol (50 ml) are refluxed overnight. The solution is filtered and concentrated to give 2.03 g (77% ) of an off white solid. The solid was used as is.
75%	With hydroxylamine hydrochloride; triethylamine; In methanol; at 20℃;Reflux;	General procedure: A solution of the appropriate cyanophenyl 1a-1k (0.1 mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was left under stirring at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3 100 mL) and dried with Na2SO4. The ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2k. Compounds 2a-2k were characterized as follows. 5.1.2. N'-Hydroxybenzimidamide (2a) White solid, yield: 75%, mp: 74-75 C (lit. 76 C 34).
75%	With hydroxylamine hydrochloride; triethylamine; In methanol; at 20 - 65℃;	General procedure: A solution of the appropriate cyanophenyl 1a-1j (0.1mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was stirred at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3×100 mL) and dried with Na2SO4. Ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2j.
70%	With hydroxylamine hydrochloride; triethylamine; In ethanol; for 7h;Reflux;	PREPARATION 13 PREPARATION OF N -HYDROXYBENZAMIDINE A mixture of benzonitrile (5.00 g, 48.5 mmol), hydroxylamine hydrochloride (8.42 g, 121 mmol) and triethylamine (30 mL) was refluxed in 30 mL of ethanol for 7 hours. After removal of solvent in vacuo, the residue (white suspension) was mixed with water and extracted with ethyl acetate (3 x 50 mL). The collected organic solution was dried over sodium sulfate. N'-hydroxybenzamidine was obtained as a grey gum in 70% yield (4.60 g) after the removal of the solvent in vacuo. 1H NMR (400 MHz, CDC13): £7.65-7.60 (m, 2H), 7.46-7.35 (m, 3H), 4.95 (br s, 2H).
66%	With hydroxylamine hydrochloride; potassium carbonate; In ethanol; for 8h;Reflux;	Method B (Gosenca et al., 2013): A solution ofbenzonitrile (3.6 mmol, 0.371 g), hydroxylamine hydrochloride (7.2 mmol, 0.50 g), and potassium carbonate (7.25 mmol, 1.0 g) were suspended in anhydrous ethanol (50 mL). The mixture was refluxed for 8 h. The precipitate was rapidly filtered off before cooling and the solvent was evaporated under vacuum. The crude product was recrystallized from dichloromethane-petroleumether to give benzamidoxime (6) (0.325 g, 66 %). Mp:63-65 C. IR (ATR), upsilon (cm-1): 3450, 3357 (NH2), 3181(N-OH), 1642 (C=N).
65.8%	With hydroxylamine hydrochloride; potassium carbonate; In ethanol; at 20℃; for 12.5h;Reflux;	General procedure: Hydroxylamine hydrochloride (200 mmol) and K2CO3(200 mmol) were dissolved in 200 mL of alcohol and stirred for30 min at room temperature. The corresponding nitriles (75 mmol)1 were added and the reaction mixture was heated to reflux for12 h. After filtration of inorganic salts, the solvent was evaporatedunder reduced pressure. The products 2 were purified by columnchromatography (petroleum ether/acetone, 2:1, v/v).
65%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).
65%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: General procedure 1.To a stirred suspension of corresponding nitrile 1 and hydroxylamine hydrochloride(1.5 equiv.) in EtOH (10 mL per gram of nitrile) NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).
65%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL). N?-Hydroxybenzimidamide (AM-2). Compound was synthesized by following GP1 starting from benzonitrile (15 g, 0.145 mol) in 65% (12.87 g) yield
65%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).
50%	With hydroxylamine hydrochloride; sodium carbonate; In water; at 20℃;	General procedure: Na2CO3 (3.61 g, 34 mmol) was dissolved in water (83 mL), and NH2OHxHCl (4.30 g, 61.4 mmol) was slowly added. After complete removing of CO2 appropriate nitrile (19 mmol) was added and mixture was stirred at room temperature for several days. Solvents were evaporated under reduced pressure to final volume of 50 mL. Obtained solution was extracted with ethylacetate (2 x 50 mL) and dried over Na2SO4. The solvent was removed at reduced pressure, to give the raw product that was finally purified by crystallization in ethyl acetate or by chromatography on SiO2, eluting with hexane/ethyl acetate (yields 20-50 %).
	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 20℃;	General procedure: To a solution of 0.01 mol of nitrile in 200 mL of ethanol was added a solution of 0.695 g (0.01 mol) of hydroxylamine hydrochloride in 10 mL of water, followed by the further addition of 0.420 g (0.005 mol) of sodium carbonate in 10 mL of water. The reaction mixture was stirred overnight at rt. The mixture was then concentrated to small volume under vacuum, diluted with cold water, and placed in refrigerator overnight. The precipitate that formed was recovered and recrystallized from ethanol. All amidoximes were known and characterized by comparison of their physical data with those prepared in accordance with literature procedures.1
	With hydroxylamine;	Benzamidoxime (N-hydroxy-benzene-carboximidamide) was synthesized from benzonitrile and hydroxylamine as previously described and was assayed as usual (Krueger, 1885).
	With hydroxylamine; In ethanol; water; for 1h;Reflux;	General procedure: 50 % Aq. Hydroxylamine (1.05 mmole) was added to a solution of nitrile (10, 1.0 mmole)in ethanol (10 vol) at room temperature. Reflux the reaction mass for 1 hr (TLC monitored).After completion of reaction, cooled to room temperature and concentrated under reducedpressure to get the corresponding amidoxime (7a-m) as a white to yellow colored solidwhich was used directly in the next step without further purification.
	With hydroxylamine; In ethanol; water; for 1.5h;Reflux; Inert atmosphere;	General procedure: To the solution of nitrile (1) in EtOH (0.1 M) was added 50wt% aqueous hydroxylaminesolution (1.2 equiv). The mixture was stirred at reflux temperature for 1.5 h under nitrogen. After cooling to room temperature, the reaction mixture was concentratedunder reduced pressure. The crude amidoxime (2) product was dissolved in CH2Cl2(0.1 M), and then ArSO2Cl (TsCl or o-NsCl, 1.05 equiv) and DIPEA (1.05 equiv)were added at 0 oC. The mixture was stirred under nitrogen atmosphere at room temperature for 3 h or at reflux temperature for 1 h (see reference 3 for details).3 Themixture was concentrated under reduced pressure. The crude cyanamide (3) productwas dissolved in the mixture of 1 N aqueous HCl solution and EtOH (1 N HCl / EtOH= 1 : 4, v/v, reaction concentration = 0.1 M). The mixture was stirred at reflux temperaturefor 3 h under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography.
	With hydroxylamine; In ethanol; water; for 2h;Reflux;	General procedure: Hydroxylamine (50% by weight in H2O, 1.32 mL, 20 mmol, 4 equiv) and the corresponding nitrile derivatives 12* (5 mmol, 1 equiv) were combined in EtOH (20 mL) and heated to reflux for 2 h. Then the reaction mixture was cooled to 23 C and was concentrated in vacuo to give the corresponding amidoxime derivatives 11* as white solids in quantitative yields.(A. R. Gangloff, J. Litvak, E. J. Shelton, D. Sperandio, V. R. Wang, K. D. Rice, Tetrahedron Lett. 2001, 42, 1441.) The analytical data of synthesized amidoxime derivatives 11* were in good correlation with literature reported data. (X. Yang, G. Liu, H. Li, Y. Zhang, D. Song, C. Li, R. Wang, B. Liu, W. Liang, Y. Jing, G. Zhao, J. Med. Chem. 2010, 53, 1015; C. Quan, M. Kurth, J. Org. Chem. 2004, 69, 1470.)
	With hydroxylamine; acetic acid; In neat (no solvent); at 150℃; for 0.666667h;	General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.
	With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; for 8h;Reflux;	General procedure: All solvents and reagents were obtained from commercialsources. All synthesized compounds were purified by chromatography and analyzed by IR, HRMS, and NMR. Purity of synthesizedcompounds was verified prior to biological tests by chromatographic analyses and NMR (see supplementary material) and in allthe cases purity was higher than 95%. IR spectra have been registered (in Nujol) with a Shimadzu FTIR-8300 spectrophotometer;melting points have been determined on a Reichart-Thermovarhotstage Kofler and are uncorrected. NMR spectra have beenregistered on a Bruker AVANCE DMX 300 using CDCl3 and DMSO assolvent. HRMS spectra were recorded by analyzing a 50 ppm solution of the compound in a 6540 UHD Accurate-Mass Q-TOF LC/MS(Agilent Technologies) equipped with a Dual AJS ESI source. GC-MSspectra have been registered by using either an Agilent 7890B/7000C GC-MS-TQ or a GC-MS Shimadzu QP-2010 Instrument. Flashchromatography was performed by using silica gel (Merck,0.040e0.063 mm) and mixtures of ethyl acetate and petroleumether (fraction boiling in the range of 40e60 C) in various ratios. 3-Methyl-benzamidoxime [31], 2-picolin-amidoxime [32],isonicotin-amidoxime [33], nicotin-amidoxime [33], and benzamidoxime [34] were synthesized as reported. Generally, an acqueous solution of hydroxylamine was prepared by mixingNH2OH*HCl (36 mmol) and NaOH (36 mmol) in water (20 mL). Thehydroxylamine solution was then added to an alcoholic solution ofthe corresponding nitrile (30 mmol) dissolved in ethanol (100 mL)in a 250 mL round bottomed flask. The mixture was refluxed for 8 h.The solvent was then removed under vacuum and 100 mL waterwere added to the residue. The amidoxime was filtered as a whitesolid and re-crystallized from ethanol.
	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 20℃;	General procedure: The amidoximes were prepared according to our previous report. 16h To a solution of the appropriate nitrile (0.01 mol) in EtOH (200 mL)was added a solution of hydroxylamine hydrochloride (0.695 g, 0.01mol) in H2O (10 mL), followed by the addition of Na2CO3 (0.420 g, 0.005 mol) in H2O (10 mL). The reaction was stirred overnight at r.t. and then concentrated to a small volume under vacuum, diluted withcold H2O, and placed in a refrigerator overnight. The precipitate that formed was recovered and recrystallized from EtOH. All the prepared amidoximes are known and were characterized by comparison of their physical data with those prepared in accordance with literature procedures.

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4
[ 2553-19-7 ]
[ 613-92-3 ]
[ 55275-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium In benzene Heating;

Reference： [1]Goel,A.B.; Gupta,V.D. [Journal of Organometallic Chemistry, 1975, vol. 85, p. 327 - 333]

5
[ 613-92-3 ]
[ 2757-23-5 ]
[ 1456-22-0 ]
[ 75465-37-1 ]
[ 110991-34-9 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 181 - 190
[2]Heterocycles,1987,vol. 26,p. 181 - 190

6
[ 81467-48-3 ]
[ 1456-22-0 ]
[ 80628-80-4 ]
[ 613-92-3 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 336 - 340

7
[ 588-22-7 ]
[ 613-92-3 ]
[ 891980-85-1 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 1495 - 1498

8
[ 613-92-3 ]
[ 19887-32-2 ]
ethyl [(S)-2-phenyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]carbamate [ No CAS ]

Reference： [1]Synthesis,2004,p. 1589 - 1594

9
[ 613-92-3 ]
[ 157373-08-5 ]
[ 740817-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In toluene for 8h; Heating;

Reference： [1]Buscemi, Silvestre; Pace, Andrea; Piccionello, Antonio Palumbo; Pibiri, Ivana; Vivona, Nicolo [Heterocycles, 2004, vol. 63, # 7, p. 1619 - 1628]

10
[ 613-92-3 ]
[ 762-42-5 ]
[ 62222-38-2 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5336 - 5339

11
[ 613-92-3 ]
[ 500-76-5 ]
4-[4-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-phenoxy]-phenol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5822 - 5826

12
[ 613-92-3 ]
[ 530-62-1 ]
[ 1456-22-0 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5412 - 5415
[2]Tetrahedron Letters,2007,vol. 48,p. 1479 - 1483

13
[ 613-92-3 ]
[ 1456-22-0 ]

Reference： [1]Journal of Chemical and Engineering Data,1987,vol. 32,p. 127 - 128
[2]Chemische Berichte,1885,vol. 18,p. 2471
Chemische Berichte,1886,vol. 19,p. 1481
[3]Journal of labelled compounds and radiopharmaceuticals,2012,vol. 55,p. 71 - 79

14
[ 613-92-3 ]
[ 1456-22-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 336 - 340

15
[ 13512-57-7 ]
[ 613-92-3 ]
[ 220050-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	A solution of (2S)-2-tert-butoxycarbonylamino-succinic acid-1-benzyl ester (2. 16G, 6. 68MMOL) in DICHLOROMETHANE (1 OML) was treated with N-hydroxy-benzamidine (1 g, 7. 34MMOL), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1. 41 G, 7. 34MMOL), 1-hydroxybenzotriazole hydrate (991 MG, 7. 34MMOL) and 4-methylmorpholine (1. 1mL, 10mmol) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with DICHLOROMETHANE (100mL) and washed with saturated sodium hydrogen carbonate solution (50mL) and brine (50mL). The organic layer was dried over magnesium sulphate, concentrated in vacuo and azeotroped with ether. The solid product was triturated with diisopropyl ether (30mL) and methanol (1. 5ML) and then RECRYSTALLISED from ethyl acetate to yield the title product ; 1HNMR (CDCI3, 400MHZ) : 1.41 (s, 9H), 1.59 (m, 2H), 3.08 (dd, 1 H), 3.20 (dd, 1 H), 5.78 (m, 1 H), 5.24 (m, 2H), 5.56 (m, 1 H), 7.37 (m, 5H), 7.48 (m, 3H), 7.69 (m, 2H); MS ES+ m/z 464 [MNa] +.

Reference： [1]Patent: WO2004/56787,2004,A1 .Location in patent: Page 58

16
[ 613-92-3 ]
[ 500-76-5 ]
4-[4-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-phenoxy]-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 0 - 110℃;	Part B 4-[4-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-phenoxy]-phenol To a stirred solution of 2-(1H-benxotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (706 mg, 2.2 mmol), 1-hydroxybenztriazole (54 mg, 0.4 mmol) and diisopropylethylamine (1.29 g, 10.0 mmol) in dimethylformamide (3.2 mL) was added a solution of N-hydroxybenzenecarboximidamide (300 mg, 2.2 mmol) and <strong>[500-76-5]4-(4-hydroxyphenoxy)benzoic acid</strong> (from Preparation 7) (460 mg, 2.0 mmol) in dimethylformamide (3.2 mL). After a few minutes, the mixture was warmed to 110 IC for 3 hours. The mixture stood overnight at 0 C. and was then diluted with ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution, and brine. The extract was dried over sodium sulfate, filtered and concentrated to a red oil that was chromatographed yielding 320 mg of the title compound as a white crystalline solid. LC-MS (m/z, APCI): 329 [M-H]-.

Reference： [1]Patent: US2004/6057,2004,A1 .Location in patent: Page/Page column 35

17
[ 26250-84-0 ]
[ 613-92-3 ]
[ 623949-95-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid; N-hydroxybenzenecarboximidamide In dichloromethane at 0℃; for 1h; Stage #2: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	4.A A solution of (S)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (0.229 g, 1.00 mmol) and N-hydroxybenzamidine (0.140 g, 1.03 mmol) in dichloromethane (10 ml) was cooled in an ice bath. After one hour HOBT (0.27 g, 2.0 mmol), NMM (0.24 ml, 2.2 mmol), and EDCl (0.25 g, 1.3 mmol) were added sequentially with stirring and the resulting yellow solution was slowly warmed to room temperature. Upon disappearance of starting materials monitored by tlc, the reaction was quenched by addition of cold water. The separated organic phase was washed with saturated NaHCO3 aqueous solution, 2 N citric acid aqueous solution, saturated NaHCO3 aqueous solution, and dried over Na2SO4. After filtration and evaporation, the residue (0.216 g of bright yellow oil) was analyzed and determined to be O-acylamidoxime of sufficient purity (HPLC: 77% (at) 254 nm, 75% (at) 214 nm) for the next reaction. MS (ES+) (relative intensity): 348.3 (100) (M+1).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2004/10014, 2004, A1 Location in patent: Page/Page column 29

18
[ 613-92-3 ]
[ 218608-98-1 ]
C₂₂H₂₆FN₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl-carbodiimide; In dichloromethane; at 20℃; for 16 - 18h;	To a mixture of 33.4 mg (0.25 mmole) of A/-hydroxybenzamidine (Example 1) and80.0mg (0.27 mmole; 1.1 eq.) of (3R)-terf-butoxycarbonylamino-4-(2-fluoro-phenyl)-butyric acid in 5 mL of dry dichloromethane is added 43.6 mg (0.27 mmole) of 1,3-di-/so-propylcarbodiimide. The mixture is stirred for 16-18 hours at room temperature under nitrogen. The progress of the reaction is monitored by TLC (Kieselgel Merck 5554 sheets, eluent: dichloroethane-ethanol 5:1). When the formation of the opened-chain intermediate is complete, the reaction mixture is evaporated to dryness

Reference： [1]Patent: WO2006/13104,2006,A1 .Location in patent: Page/Page column 29-30

19
1,2-diamino-2-methlypropane [ No CAS ]
[ 613-92-3 ]
[ 207557-35-5 ]
(2S)-1-[1,1-Dimethyl-2-(3-phenyl-[1,2,4]oxadiazol-5-ylamino)-ethylamino]-acetyl}-pyrrolidine-2-carbonitrile, methanesulfonic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate;	Example 173 (2S)-1-[1,1-Dimethyl-2-(3-phenyl-[1,2,4] oxadiazol-5-ylamino)-ethylamino]-acetyl}-pyrrolidine-2-carbonitrile, Methanesulfonic Acid Salt This compound was obtained in analogy to example 172, steps B] to D] starting from N-hydroxy-benzamidine, 1,2-diamino-2-methlypropane and IIA. The residue obtained by flash chromatography was dissolved in ethyl acetate and precipitated by treatment with methanesulfonic acid yielding a white powder. MS (ISP): 369.4 (MH+).

Reference： [1]Patent: US2003/130281,2003,A1

20
[ 613-92-3 ]
[ 161660-94-2 ]
tert-butyl {(1S,3R)-3-[([(1Z)-amino(phenyl)methylene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 21h;	EXAMPLE 6; jV-[(15,,3i?)-3-(3-phenyl-l,2,4-oxadiazol-5-yl)cyclopentyl]-l//-pyrazolo[3,4-cT]pyrimidin-4-amine; Step A: tert-buty\\ {(IS,3R)-H([(1Z)-amino(phenyl)methylene]amino}oxy)carbonyl]cyclopentyl}carbamate; To a solution of (l/?,3.S)-3-[(/er/'-butoxycarbonyl)amino]cyclopentanecarboxylic acid (500 mg, 2.18 mmol) in methylene chloride (10 mL) at room temperature was added HOBt (334 mg, 2.18 mmol), EDC (472 mg, 2.29 mmol) and JV-hydroxybenzenecarboximidamide (327 mg, 2.40 mmol). After 21 h, the reaction was poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (50percent ethyl acetate / hexanes - 100percent ethyl acetate / hexanes) gave the title compound (600 mg) as a white solid. MS 348 (M+tT); 'H NMR (400 MHz, DMSO-d6): 7.70 (d, J= 7.4 Hz, 2H), 7.50-7.43 (m, 3H), 6.89 (d, J= 12 Hz, 1H), 6.74 (s, 2H), 3.80 (m, 1H), 2.97-2.93 (m, 1H), 2.22-2.19 (m, 1H), 1.90-1.80 (m, 3H), 1.65-1.47 (m,2H), 1.38 (s,9H).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 41-42

21
[ 161601-29-2 ]
[ 613-92-3 ]
tert-butyl {(1S,3S)-3-[([(1Z)-amino(phenyl)methylene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;	EXAMPLE 7; A^-[(l1S',3iS,)-3-(3-phenyl-l,2,4-oxadiazol-5-yl)cyclopentyl]-l//-pyrazolo[3,4-</]pyrimidin-4-amine; Step A: terf-butyl {(1S,3S>3-[([(1Z)-amino(phenyl)methylene]amino}oxy)carbonyl]cyclopentyl}carbamate; To a solution of (lS^S^-Kte^butoxycarbonytyaminoJcyclopentanecarboxylic acid (200 mg, 0.872 mmol) in methylene chloride (10 mL) at room temperature was added HOBt (134 mg, 0.872 mmol), EDC (189 mg, 0.916 mmol) and 7V-hydroxybenzenecarboximidamide (131 mg, 0.960 mmol). After 3 h, the reaction was poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (30% ethyl acetate / hexanes -> 100% ethyl acetate / hexanes) gave the title compound (277 mg) as a white solid. MS 348 (M+l); 'HNMR(300 MHz, DMSO-4): 7.71-7.68 (m, 2H), 7.50-7.41 (m, 3H), 6.91 (d, J= 6.6 Hz, 1H), 6.75 (s, 2H), 3.88 (m, 1H), 3.12-3.07 (m, 1H), 2.05-L43 (m, 6H), 1.32 (s, 9H).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 44

22
[ 1477-49-2 ]
[ 613-92-3 ]
[ 1023731-28-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 513 - 539

23
[ 135072-15-0 ]
[ 613-92-3 ]
[ 1131220-55-7 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a stirred solution of <strong>[135072-15-0]4-benzyl-2-morpholinecarboxylic acid hydrochloride</strong> (intermediate 20, 1.5 g, 5.82 mmol) in N,N-dimethylformanide (10 ml) was added 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluroniumtetrafluoroborate (2.2 g, 6.98 mmol), 1-hydroxybenzotriazole hydrate (236 mg, 1.74 mmol) and N,N-diisopropylethylamine (5.1 ml, 29.1 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. After the addition of N'-hydroxybenzamidine (792 mg, 5.82 mmol), the reaction mixture was stirred at room temperature for one hour, and then heated to 110 C. When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel, (eluentl 25 % ethyl acetate in hexane) to afford 4-benzyl-2-(3-phenyl-l,2,4-oxadiazol-5-yl)morpholine (intermediate 2JL, 1.44 g, 77 %) as a colorless oil.IH NMR (400 MHz, CDCl3) ? : 2.41-2.47(1H, m), 2.6O(1H, dd, J=9.8, 11. IHz), 2.73(1H, dd, J=1.2, 11.7 Hz), 3.13(1H, d, J=11.7 Hz), 3.6l(2H, s), 3.85-3.9l(lH, m), 4.11(1H, dt, J=3.0, 11.5 Hz), 4.99(1H, dd, J=2.8, 9.4 Hz), 7.26-7.38(5H, m), 7.45-7.52(3H, m), 8.09-8.12(2H, m) MS: [M+H]+= 322

Reference： [1]Patent: WO2009/35159,2009,A1 .Location in patent: Page/Page column 22-23

24
[ 135072-15-0 ]
[ 613-92-3 ]
[ 1131220-55-7 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a stirred solution of 4-benzyl"2-morpholinecarboxylic acid hydrochloride (intermediate 20, 1.5 g, 5.82 mmol) in N,N-dimethylformanide (10 ml) was added 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluroniumtetrafluoroborate (2.2 g, 6.98 mmol), 1-hydroxybenzotriazole hydrate (236 mg, 1.74 mmol) and N,N-diisopropylethylamine (5.1 ml, 29.1 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. After the addition of N'-hydroxybenzamidine (792 mg, 5.82 mmol), the reaction mixture was stirred at room temperature for one hour, and then heated to 110 C. When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel, (eluent; 25 % ethyl acetate in hexane) to afford 4-benzyl-2-(3-phenyl-l,2,4-oxadiazol-5-yl)morpholine (intermediate 21, 1.44 g, 77 %) as a colorless oil. m NMR (400 MHz, CDCl3) delta : 2.41-2.47(1H, m), 2.60(lH, dd, J=9.8, 11. IHz), 2.73(1H, dd, J=1.2, 11.7 Hz), 3.13(1H, d, J=11.7 Hz), 3.6l(2H, s), 3.85-3.9l(lH, m), 4.1l(lH, dt, J=3.0, 11.5 Hz), 4.99(1H, dd, J=2.8, 9.4 Hz), 7.26"7.38(5H, m), 7.45-7.52(3H, m), 8.09-8.12(2H, m) MS: [M+H]+= 322

Reference： [1]Patent: WO2009/35162,2009,A1 .Location in patent: Page/Page column 22-23

25
[ 501-00-8 ]
[ 613-92-3 ]
[ 1165931-58-7 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5640 - 5643

26
[ 91004-48-7 ]
[ 613-92-3 ]
C₁₆H₁₅N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4,5-Dimethoxy-3-nitrobenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; Stage #2: N-hydroxybenzenecarboximidamide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;

Reference： [1]Kiss, László E.; Ferreira, Humberto S.; Torrão, Leonel; Bonifácio, Maria João; Palma, P. Nuno; Soares-Da-Silva, Patrício; Learmonth, David A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3396 - 3411]

27
[ 348-36-7 ]
[ 613-92-3 ]
[ 1253493-44-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4523 - 4530

28
[ 67929-86-6 ]
[ 613-92-3 ]
[ 1253493-38-7 ]

Yield	Reaction Conditions	Operation in experiment
37%	Stage #1: N-hydroxybenzenecarboximidamide With sodium ethanolate In ethanol at 20℃; for 0.5h; Stage #2: methyl 5-methoxyindole-2-carboxylate In ethanol Reflux;

Reference： [1]Location in patent: experimental part Ziedan, Noha I.; Stefanelli, Fabio; Fogli, Stefano; Westwell, Andrew D. [European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4523 - 4530]

29
[ 1486-51-7 ]
[ 613-92-3 ]
[ 1136832-85-3 ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: p-(benzyloxy)benzoic acid; N-hydroxyl-benzamidine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃;	EDC (299 mg, 1.54 mmol) in CH2Cl2 (5.0 mL) was added to a solution of 4-benzyloxybenzoic acid (336, 1.47 mmol) and benzylhydroxyamidine (200 mg, 1.47 mmol) in CH2Cl2 (5.0 mL). The mixture was stirred for 6 hours and checked by TLC for completion. Then tetrabutylammonium fluoride (1.0 M in THF, 2.95 mL) was added dropwise and the solution was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure and the product was purified by column chromatography over silica gel (EtOAc/Hex (:4→1:2) and was crystallized from hot ethyl acetate to give a white crystalline material (107 mg, 22%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.16 (2H, s), 7.11 (2H, d, J=8.8 Hz), 7.36-7.46 (5H, m), 7.49-7.51 (3H, m), 8.16 (4H, d, J=8.6 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 70.4 (CH2), 115.5 (CH), 117.3, 127.3, 127.7 (CH), 127.8 (CH), 128.5 (CH), 128.9, 129.0 (CH), 130.3 (CH), 131.3, 136.2, 162.5, 169.0, 175.8. MS (FAB+): 329 (MH+). HRMS for C21H16N2O2 (MH+): calculated: 329.1290; found 329.1302.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF NOTRE DAME DU LAC - US2010/261673, 2010, A1 Location in patent: Page/Page column 9

30
[ 613-92-3 ]
[ 693-13-0 ]
[ 4128-37-4 ]
[ 1031930-61-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With oxygen In toluene for 6h; Reflux; Air atmosphere;

Reference： [1]Location in patent: experimental part Ispikoudi, Maria; Amvrazis, Michalis; Kontogiorgis, Christos; Koumbis, Alexandros E.; Litinas, Konstantinos E.; Hadjipavlou-Litina, Dimitra; Fylaktakidou, Konstantina C. [European Journal of Medicinal Chemistry, 2010, vol. 45, # 12, p. 5635 - 5645]

31
[ 13734-41-3 ]
[ 613-92-3 ]
[ 1176166-54-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dmap; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 24h;	2.2.1. 2-(N-tert-Butoxycarbonylamino)-3-methyl-O-butyrylbenzamidoxime (4) Benzamidoxime (2) (1.21 g, 8.9 mmol) was dissolved in anhydrous acetonitrile. After addition of N-t-butoxycarbonyl-l-valine (2.60 g, 12.0 mmol), 4-DMAP (0.15 g, 0.80 mmol) and DCC the solution was stirred for 24 h at room temperature. The solvent was evaporated under reduced pressure and the crude product was recrystallized from H2O/EtOH (1/3, v/v). Yield 86%; mp: 147 °C; IR (KBr): ν 3496, 2928, 1744, 1686, 1612, 1392, 1374 cm-1; 1H NMR (DMSO-d6): δ 0.83 (d, 6H, 3J = 6.4, CH3), 1.40 (s, 9H, CH3), 2.08 (m, 1H, CH(CH3)2), 4.05 (t, 1H, 3J = 8.0, CH-NH), 6.85 (s, 2H, NH2), 7.31 (d, 1H, 3J = 9.2, NH), 7.44 (m, 3H, Ar-H), 7.52 (m, 2H, Ar-H); 13C NMR (DMSO-d6): δ 18.3, 19.0, 28.2, 30.1, 59.1, 78.3, 126.7, 128.3, 130.5, 131.4, 155.7, 157.0, 168.9; LRMS (ESI) m/z: 693 [2M+Na]+, 336 [M+H]+, 280 [M-(CH3)2CCH2+H]+, 137 [BAO+H]+, 118 [Val+H]+; Anal. Calcd for C17H25N3O4 (335.41): C, 60.88; H, 7.51; N, 12.53. Found: C, 60.96; H, 7.71; N, 12.63.

Reference： [1]Location in patent: experimental part Kotthaus, Joscha; Hungeling, Helen; Reeh, Christiane; Kotthaus, Jürke; Schade, Dennis; Wein, Silvia; Wolffram, Siegfried; Clement, Bernd [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 1907 - 1914]

32
[ 613-92-3 ]
[ 1670-14-0 ]

Yield	Reaction Conditions	Operation in experiment
94.1%	With ammonia; hydrogen; In methanol; at 50℃; under 15001.5 - 22502.3 Torr;Autoclave;	Benzal oxime (272 g, 2.0 mol, 1.0 eq), methanol (500 mL) and Raney Ni (15 g) were charged into a 1 L autoclave. A small amount of liquid ammonia was charged and N2 was substituted three times. H2 was then added to maintain the autoclave Pressure 2-3MPa, temperature control 50 , the reaction until no longer hydrogen absorption, after the end of the reaction, filtration, the filtrate was concentrated to dryness, the residue was cooled to 5 , the solid precipitation, filtration, to get gray crude benzamidine hydrochloride , Then add ethanol (700mL) heated completely dissolved, then add activated carbon bleaching, refluxing 30min, filtered while hot, cooled to 0 C, filtered and dried at 50 C in vacuo to give a white solidBenzamidine hydrochloride 325 g, yield 94.1%, HPLC purity 99.6%.

Reference： [1]Patent: CN107353230,2017,A .Location in patent: Paragraph 0023; 0025; 0026; 0027; 0030; 0031
[2]Synthetic Communications,2011,vol. 41,p. 2195 - 2199
[3]Antimicrobial Agents and Chemotherapy,2015,vol. 59,p. 890 - 904

33
[ 19227-13-5 ]
[ 613-92-3 ]
[ 1313498-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃;	Add benzamidoxime (5.63 g, 41.36 mmol) to a 1M solution of potassium t-butoxide (31 mL, 31 mmol) in tetrahydrofuran and anhydrous tetrahydrofuran (442 mL). Add methyl 2-oxopiperidine-4-carboxylate (5 g, 31.8 mmol) and stir overnight at room temperature. Pour reaction over saturated aqueous sodium bicarbonate and extract into chloroform. Separate layers and extract the aqueous phase with additional chloroform. Dry the combined organic layers over anhydrous magnesium sulfate, filter, and concentrate to dryness under reduced pressure. Purify the resulting residue by flash chromatography (silica gel), eluting with 1 -5% 7 N ammoniated methanol indichloromethane to afford the title compound (4.15 g). *H NMR (CDC13) δ 2.19 (m, 1 H), 2.34 (m, 1H), 2.8-2.95 (m, 2H), 3.44-3.52 (m, 2H), 3.57 (m, 1H), 6.13 (bs, 1H), 7.45-7.54 (m, 3H), 8.0-8.11 (m, 2H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2011/82010, 2011, A1 Location in patent: Page/Page column 20

34
[ 13222-85-0 ]
[ 613-92-3 ]
[ 16112-24-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	In water; for 12h;Reflux;	General procedure: The amidoxime (10 mmol) and anhydride (11 mmol) was added to water (20 mL) and the solution was stirred for 12 h at reflux. After stirring, the reaction mixture was washed with diethyl ether (3x50 mL). The resulting mixture was subjected to column chromatography on silica gel with EtOAc/n-hexane (1:9) and evaporation of the solvent under reduced pressure gave pure products in 35-93% yields. All products gave satisfactory spectral data in accord with the assigned structures.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 6424 - 6426

35
[ 613-92-3 ]
[ 129765-95-3 ]
[ 1426444-02-1 ]

Yield	Reaction Conditions	Operation in experiment
67.5%		A solution of 3-(tert-butoxycarbonylamino)-3-methylbutanoic acid (2.75 g, 12.7 mmol) and ?,?'-carbonyldiimidazole (CDI; 2.05 g, 12.7 mmol) in DMF (20.0 mL) was stirred at RT under nitrogen atmosphere for 5 h. N-Hydroxybenzamidine (1.72 g, 12.7 mmol) was added and the reaction mixture was heated to 100 C and stirred for 15 h. The crude reaction mixture was concentrated in vacuo, poured into ethyl acetate (100 mL) and extracted with water (3 x 100 mL). The combined aqueous layer was back-extracted with ethyl acetate (100 mL). The combined organic layer was dried over MgS04, concentrated in vacuo and purified by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) to yield the product as white solid (2.72 g, 8.57 mmol, 67.5 %). MS: M = 318.1 (M+H)+

Reference： [1]Patent: WO2013/34506,2013,A1 .Location in patent: Page/Page column 46

36
[ 613-92-3 ]
[ 126501-70-0 ]
[ 280110-59-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Example 17A2 2,2,2-trifluoro- 1 -(4-(3-phenyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)ethanone To a solution of Example 17A1 (3 g , 133mmol) in dichloromethane (60 mL) was added (Z)-N'-hydroxybenzimidamide (2g) and N-(3-dimethylaminopropyl)-N'- ethylcarbodiimide hydrochloride (3.06g). The resulting mixture was stirred at room temperature overnight. The reaction mixture was washed with saturated brine, dried (MgS04), filtered, and concentrated and the crude product was purified by column chromatography on silica gel to give Example 17A2 in 80% yield as a white solid. MS m/z 326 (M+H)+.

Reference： [1]Patent: WO2013/10453,2013,A1 .Location in patent: Page/Page column 109

37
[ 613-92-3 ]
[ 530-62-1 ]
[ 1456-22-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	In acetonitrile; for 5h;Reflux;	Intermediate VIII-1; 3-Phenyl-4H-[l,2,4]oxadiazol-5-one To a solution of N-hydroxy-benzamidine (5.0 g, 36.7 mmol) in acetonitrile (150 mL) was added 1,1 '- carbonyldiimidazole (6.55 g, 40.5 mmol). The reaction mixture was heated to reflux for five hours, cooled down to RT, concentrated under vacuo and purified by column chromatography (EtO Ac/Heptane 4/1) to give 3.8 g (64%) of the title product as a white solid.

Reference： [1]Patent: WO2015/140130,2015,A1 .Location in patent: Page/Page column 149
[2]Turkish Journal of Chemistry,2014,vol. 38,p. 56 - 62

38
[ 613-92-3 ]
[ 192945-49-6 ]
[ 1630015-51-8 ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 1921 - 1930

39
[ 473416-12-5 ]
[ 613-92-3 ]
[ 1630015-55-2 ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 1921 - 1930

40
[ 5471-82-9 ]
[ 613-92-3 ]
[ 1630015-67-6 ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 1921 - 1930

41
[ 22651-87-2 ]
[ 613-92-3 ]
[ 938020-91-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	In neat (no solvent); at 80℃; for 0.1h;Green chemistry;	A mixture of benzamidoxime (1.47 mmol), <strong>[22651-87-2]cyclohexanecarboxylic acid anhydride</strong> (1.77 mmol) and HClO4-SiO2 (5 mol%) was stirred at 80 C for 6 min. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature, diluted with dichloromethane (5 mL) and the catalyst was allowed to settle down. Then the reaction mixture was filtered, washed with dichloromethane (5 mL), and the combined organic layers were washed with saturated aq. NaHCO3 and water. The obtained organic layer was dried over anhy. Na2SO4 and concentrated under reduced pressure to get crude compound. The crude was then purified by column chromatography on silica gel using hexane/EtOAc (8:2) as eluents to get pure compound 5i.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 1978 - 1986

42
[ 19887-32-2 ]
[ 613-92-3 ]
[ 403860-20-8 ]

Reference： [1]Patent: WO2014/110298,2014,A1

43
[ 19887-32-2 ]
[ 613-92-3 ]
ethyl [(S)-2-phenyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; In 1,4-dioxane; at 100℃; for 16h;	N,N”-dicyclohexylcarbodiimide (454 mg, 2.2 mmol) was added to a solution of benzamidooxime (272 mg, 2 mmol) and N-ethyoxycarbonyl-L-phenylalanine (475 mg, 2 mmol) in 1,4-dioxane (20 mL). The reaction mixture was heated under stirring at 100 c for 16 hours. The solyent was remoyed under yacuum and the residue purified by silica gel chromatography eluting with EtOAc / hexanes to afford 280 mg of (S)-ethyl 2-phenyl-1-(3-phenyl-1,2,4- oxadiazol-5-yl)ethylcarbamate which was dissolyed in 10 m of ethanol and 10 m of 10% NaOH aqueous solution. The mixture was heated up to 100 c for 3 hours, and then cooled down to ambient temperature. After extracted with methylene chloride, the organie layer was separated and dried oyer sodium sulfate, filtered and concentrated to afford the desired product.

Reference： [1]Patent: WO2014/110298,2014,A1 .Location in patent: Paragraph 0213; 0214
[2]Journal of Chemistry,2019,vol. 2019

44
[ 613-92-3 ]
[ 51077-14-6 ]
(S)-tert-butyl 2-((benzimidamidooxy)carbonyl)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step A: PyBOP (2.53 g, 4.85 mmol) was added to a 000 solution of Boc-L-azetidine-2- carboxylic acid (650 mg, 3.23 mmol) and DIPEA (1.66 mL, 9.69 mmol) in DCM (14 mL) and the rxn mixture was stirred at rt for 20 mm, before N?-hydroxybenzimidamide (440 mg, 3.23 mmol)was added and stirring continued at rt for 2h. To the rxn mixture was added H20 and the mixture extracted with DCM (2x). The combined org. extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to yield (S)-tert-butyl 2- ((benzimidam idooxy)carbonyl)azetidine- 1 -carboxylate B-I-I which was used further without purification.

Reference： [1]Patent: WO2014/141065,2014,A1 .Location in patent: Page/Page column 49

45
[ 613-92-3 ]
[ 119757-51-6 ]
10-(trifluoromethyl)-2,3,7,12,13-pentakis(4-(trifluoromethyl)phenyl)benzo[de]isoquinolino[2,1-a][1,8]naphthyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 9889 - 9892,4
Angew. Chem.,2014,vol. 126,p. 10047 - 10050,4
Angewandte Chemie,2014,vol. 126,p. 10047 - 10050,4

46
[ 23975-15-7 ]
[ 613-92-3 ]
4,5,8,9,13-penta(thiophen-2-yl)benzo[de]thieno[2',3':3,4]pyrido[2,1-a][1,8]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper diacetate In tert-Amyl alcohol at 130℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube;

Reference： [1]Jayakumar, Jayachandran; Parthasarathy, Kanniyappan; Chen, Yi-Hsiang; Cheng, Chien-Hong; Lee, Tai-Hua; Chuang, Shih-Ching [Angewandte Chemie - International Edition, 2014, vol. 53, # 37, p. 9889 - 9892,4][Angew. Chem., 2014, vol. 126, # 37, p. 10047 - 10050,4][Angewandte Chemie, 2014, vol. 126, # 37, p. 10047 - 10050,4]

47
[ 52833-94-0 ]
[ 613-92-3 ]
N'-((2-amino-5-bromonicotinoyl)oxy)benzimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	PREPARATION 14 PREPARATION OF N'-((2- YL)oxY)BENziMiD AMIDE To a mixture of N'-hydroxybenzamidine (0.50 g, 3.68 mmol) and 2- amino-5-bromopyridine-3-carboxylic acid (0.83 g, 4.05 mmol) in 30 mL of dichloromethane was added l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.45 g, 7.36 mmol). The resulting mixture was stirred at ambient temperature overnight. After removal of solvent in vacuo, the residue was purified by column chromatography eluted with 5percent methanol in dichloromethane to afford a yellow oil which was treated with dichloromethane and ethyl ether to afford N'-((2-amino-5-bromonicotinoyl)oxy)- benzimidamide as a yellow solid in 32percent yield (0.25 g). 1H NMR (400 MHz, DMSO- d6): £8.61 (d, J= 2.4 Hz, 1H), 8.25 (d, J= 2.4 Hz, 1H), 7.74-7.70 (m, 2H), 7.52-7.42 (m, 3H), 7.34 (br s, 2H), 7.04 (br s, 2H).

Reference： [1]Patent: WO2015/81257,2015,A2 .Location in patent: Page/Page column 77

48
[ 35212-85-2 ]
[ 613-92-3 ]
C₁₆H₁₁N₃OS [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 19271 - 19279

49
[ 1036380-75-2 ]
[ 613-92-3 ]
C₁₈H₁₄BrN₃O₅S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 80 °C 2: triethylamine / dichloromethane

Reference： [1]Sinha, Shweta; Sravanthi; Yuvaraj; Manju; Doble, Mukesh [RSC Advances, 2016, vol. 6, # 23, p. 19271 - 19279]

50
[ 1036380-75-2 ]
[ 613-92-3 ]
C₁₆H₁₀BrN₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate In ethanol at 80℃;

Reference： [1]Sinha, Shweta; Sravanthi; Yuvaraj; Manju; Doble, Mukesh [RSC Advances, 2016, vol. 6, # 23, p. 19271 - 19279]

51
[ 613-92-3 ]
[ 75-05-8 ]
[ 823-94-9 ]
[ 888-71-1 ]
[ 1198-98-7 ]

Yield	Reaction Conditions	Operation in experiment
26%; 19%; 53%	at 100℃; under 7500750 Torr; for 6h;	General procedure: The Barostattype7 setup suitable for studies at pressures below 15 Kbar was used inthis work. A solution of amidoxime 1a (300 mg, 2.2 mmol) in acetonitrilewas prepared in a fluoroplastic 1.5 cm3 tube. The tube was placed in ahigh-pressure block. The block with inserted plungers, compactions, anda heater was mounted in a barostat. The pressure in the system was raisedto 10 Kbar. The reaction mixture was kept under specified conditions (seeTable 1). After the end of the experiment, the block was cooled down, thepressure was decreased to atmospheric, and the reaction mixture wasremoved from the block. The volatiles were evaporated under reducedpressure, the residue was subjected to column chromatography (SiO2,ethyl acetate-hexane, 1:4) or crystallization from ethanol or hexane

Reference： [1]Mendeleev Communications,2016,vol. 26,p. 264 - 265

52
[ 89-91-8 ]
[ 613-92-3 ]
5-(dimethoxymethyl)-3-phenyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In neat (no solvent); at 100℃; for 6h;	General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.5-(Dimethoxymethyl)-3-phenyl-1,2,4-oxadiazole (7a): Colourlessoil; yield: 0.409 g (93%); IR (KBr) (numax/cm-1): 1575, 1529, 1473,1446, 1341, 1285, 1195, 1119, 1067 (C - O), 984, 904, 787, 724, 693;1H NMR (400.1 MHz, CDCl3): delta 3.54 (s, 6H, 2 × OCH3), 5.73 (s, 1H,CH), 7.46-7.56 (m, 3H, 3 × CH), 8.14 (dd, J = 7.6, 1.2 Hz, 2H, 2 × CH);13C NMR (100.6 MHz, CDCl3): delta 54.4, 96.6, 126.8, 128.2, 129.4, 132.0,168.9, 174.9; EI-MS: m/z (%) = 220 ([M]+, 34), 190 (42), 161 (20), 118(12), 75 (100), 51 (6). Anal. calcd for C11H12N2O3 (220.23): C, 59.99; H,5.49; N, 12.72; found: C, 60.19; H, 5.57; N, 12.49%.

Reference： [1]Journal of Chemical Research,2016,vol. 40,p. 314 - 317

53
[ 613-92-3 ]
[ 6065-82-3 ]
5-(diethoxymethyl)-3-phenyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In neat (no solvent); at 100℃; for 6h;	General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

Reference： [1]Journal of Chemical Research,2016,vol. 40,p. 314 - 317

54
[ 178752-79-9 ]
[ 613-92-3 ]
5-(3-N,N-dimetylaminophenyl)-3-phenyl-4,5-dihydro-1,2,4,5-oxadiazaborole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In benzene;Reflux;	General procedure: Benzamidoxime (6) (22 mmol, 3.0 g) and phenylboronic acid (22mmol, 2.86 g) were dissolved in benzene (150mL) and the solution was refluxed overnight, then the solvent was evaporated under reduced pressure. The residual was crystallizedfrom hexane to give 3,5-diphenyl-4,5-dihydro-1,2,4,5-oxadiazaborole (7g) (4.57 g, 94 %).

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 1794 - 1812

55
[ 212650-43-6 ]
[ 613-92-3 ]
C₁₇H₂₃N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		General procedure: Step 1: To a stirred solution of N,N-carbonyldiimidazole (3.3 g,20.5 mmol) in acetonitrile compound 13 (4.3 g, 18.6 mmol) wasadded. The mixture was stirred at 45 C for 1 h, and then correspondingcarboximidamide (21.4 mmol) was added. The reactionmixture was stirred overnight at room temperature. The solventwas evaporated under reduced pressure to get a mixture of productand imidazole in quantitative yield which was used in the next stepas is.

Reference： [1]Tetrahedron,2017,vol. 73,p. 750 - 757

56
[ 121-98-2 ]
[ 613-92-3 ]
[ 36364-17-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide In dimethyl sulfoxide at 20℃; for 16h;	4.2. General procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C.

Reference： [1]Baykov, Sergey; Sharonova, Tatyana; Shetnev, Anton; Rozhkov, Sergey; Kalinin, Stanislav; Smirnov, Alexey V. [Tetrahedron, 2017, vol. 73, # 7, p. 945 - 951]

57
[ 610-96-8 ]
[ 613-92-3 ]
[ 77774-27-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 4h;	General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C.

Reference： [1]Tetrahedron,2017,vol. 73,p. 945 - 951

58
[ 611-13-2 ]
[ 613-92-3 ]
[ 309734-72-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 4h;	General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C.

Reference： [1]Tetrahedron,2017,vol. 73,p. 945 - 951

59
[ 37619-24-2 ]
[ 613-92-3 ]
5-(1-methyl-1H-pyrrol-2-yl)-3-phenyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 4h;	General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C.

Reference： [1]Tetrahedron,2017,vol. 73,p. 945 - 951

60
[ 6326-27-8 ]
[ 613-92-3 ]
[ 3213-95-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; copper(II) oxide In dimethyl sulfoxide at 110℃; for 18h;	4 Synthesis of 5- (4- (methyl) phenyl) -3- (phenyl) -1H-1,2,4-triazole, comprising the steps of: A, 0.5 mmol p-methylbenzamidine hydrochloride and 0.6 mmol N-hydroxyphenylcarboximide were placed in the reaction tube,And further adding 0.05 mmol of CuO,1.0 mmol Na2CO3 and 3 mL DMSO,The reaction was stirred at 110 ° C for 18 hours;B, the product was extracted with ethyl acetate,Dried over anhydrous sodium sulfate,Concentrated under reduced pressure,The crude product was purified by silica gel column chromatography (solvent volume ratio petroleum ether: ethyl acetate = 5: 1)(4- (methyl) phenyl) -3- (phenyl) -1H-1,2,4-triazole as a white solid,The yield was 90% and the melting point was 187-188 ° C.

Reference： [1]Current Patent Assignee: ANHUI NORMAL UNIVERSITY - CN106632106, 2017, A Location in patent: Paragraph 0076; 0077; 0078; 0079; 0080; 0081

61
[ 3261-87-8 ]
[ 613-92-3 ]
C₁₁H₁₂N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 20℃; for 2h;	General procedure: To a solution of amidoxime 1 (2.5 mmol) in DMSO (2-3 mL) a cyclic anhydride 2 (2.5 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. Next, to the reaction mixture powdered NaOH (5 mmol) was rapidly added and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was then diluted with cold water (30 mL) followed by the addition of hydrochloric acid to pH ~1. The resulting precipitate was filtered off, washed with cold water (25 mL) and dried in air at 50 C.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3672 - 3677

62
[ 613-92-3 ]
[ 62222-38-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1713 - 1726

63
[ 613-92-3 ]
[ 530-62-1 ]
[ 1456-22-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 110℃; for 16h;	To a stirred solution of N-hydroxybenzamidine (2.0 g, 14.69 mmol) in dioxane (10 mL) was added1 ,8-diazabicyclo[5.4.0]undec-7-ene (2.46 g, 16 mmol, 2.44 mL) and 1,1 ?-carbonyldiimidazole (3.57 g, 22mmol). The mixture was stirred at 110 C for 16 h, then cooled and quenched with water (10 mL). The mixture was extracted with dichloromethane (50 mL x 4), then the combined organic phases were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give crude product that was purified by chromatography (silica, petroleumether : ethyl acetate 1:1) to give 3-phenyl-1 ,2,4-oxadiazol-5(4H)-one (1 .30 g, 8.02 mmol, 55 %) as a yellow solid. 1H NMR (400 MHz, Methanol-d4) O 7.83-7.75 (m, 2H), 7.66-7.52 (m, 3H); LOMS (ESI) m/z 163.2 [M÷H]÷.

Reference： [1]Patent: WO2018/81167,2018,A1 .Location in patent: Page/Page column 96; 97
[2],

64
[ 2124-55-2 ]
[ 613-92-3 ]
C₁₆H₁₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of carboxylic acid 1 (1.1 mmol) in dry DMSO (0.5-1 mL) CDI (195 mg, 1.2 mmol) was added. The reaction mixture was stirred at room temperature for 30 min, then amidoxime 2 (1.0 mmol) was added. The reaction mixture was stirred at room temperature for another 18 h, then to the reaction mixture powdered NaOH (1.2 mmol) was added rapidly. The reaction mixture was stirred at room temperature for 2 h. Then the reaction mixture was diluted with cold water (30 mL). The resulting precipitate was filtered off, washed with cooled water (25 mL) and dried in air at 50 C.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 2824 - 2827

65
[ 1885-14-9 ]
[ 613-92-3 ]
[ 1456-22-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; In water; at 100℃; for 2h;Green chemistry;	N-hydroxybenzimidamide (1 mmol), 10 mL of water, and alkaline reagent DMAP (2 mmol) were added to a 25mL two-necked flask, and phenyl chloroformate (1.5 mmol) was added dropwise to the flask while stirring, andthe mixture was heated to reflux at 100 C. The reaction was carried out for 2 h, and the reaction wascompleted. The mixture was stirred and cooled to room temperature. The pH of the reaction system wasadjusted to 3 to 4 with 1 mol/L of dilute HCl. The solid was precipitated, filtered, and washed with water (15mL×3). Diazole derivative, yield 85%.

Reference： [1]Patent: CN108997252,2018,A .Location in patent: Paragraph 0018-0019; 0025-0034

66
[ 108-23-6 ]
[ 613-92-3 ]
[ 1456-22-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; In water; at 100℃; for 2h;Green chemistry;	General procedure: N-hydroxybenzimidamide (1 mmol), 10 mL of water, and alkaline reagent DMAP (2 mmol) were added to a 25mL two-necked flask, and phenyl chloroformate (1.5 mmol) was added dropwise to the flask while stirring, andthe mixture was heated to reflux at 100 C. The reaction was carried out for 2 h, and the reaction wascompleted. The mixture was stirred and cooled to room temperature. The pH of the reaction system wasadjusted to 3 to 4 with 1 mol/L of dilute HCl. The solid was precipitated, filtered, and washed with water (15mL×3). Diazole derivative, yield 85%.

Reference： [1]Patent: CN108997252,2018,A .Location in patent: Paragraph 0019; 0021-0022

67
[ 24608-52-4 ]
[ 613-92-3 ]
[ 1456-22-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; In water; at 100℃; for 2h;Green chemistry;	General procedure: N-hydroxybenzimidamide (1 mmol), 10 mL of water, and alkaline reagent DMAP (2 mmol) were added to a 25mL two-necked flask, and phenyl chloroformate (1.5 mmol) was added dropwise to the flask while stirring, andthe mixture was heated to reflux at 100 C. The reaction was carried out for 2 h, and the reaction wascompleted. The mixture was stirred and cooled to room temperature. The pH of the reaction system wasadjusted to 3 to 4 with 1 mol/L of dilute HCl. The solid was precipitated, filtered, and washed with water (15mL×3). Diazole derivative, yield 85%.

Reference： [1]Patent: CN108997252,2018,A .Location in patent: Paragraph 0019; 0023-0024

68
[ 19887-32-2 ]
[ 613-92-3 ]
C₁₉H₂₁N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: In a sealed tube in amicrowave reactor, 0.8 mmol of L-N-protected amino acid(1-5) and DCC (0.96 mmol, 0.199 g) were dissolved in acetone(1.0 mL) and the mixture was magnetically stirred forapproximately 40 minutes to form the reactive intermediate. Then, 0.8 mmol of aryl amidoxime (a-e) was added, and themixture was homogenized. The acetone was removed inroute evaporator without heating, and H2O (1.0 mL) wasadded to the mixture, which was subjected to microwaveirradiation at 100W power, temperature of 115C, during15 min. Soon after, the reaction crude was dissolved in ethylacetate and washed with water. The organic phase was driedover magnesium sulfate, and the solvent was removed undervacuum. The residue was purified by column chromatographyon silica gel (hexane-ethyl acetate, 7 : 3) to afford pureproducts (1-5a-e). Detailed experimental procedures, 1Hand 13C NMR spectra for all compounds, are available in thesupporting information, ESI (available here).

Reference： [1]Journal of Chemistry,2019,vol. 2019

69
[ 613-92-3 ]
[ 616-38-6 ]
[ 1456-22-0 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 11232 - 11244

70
[ 541-47-9 ]
[ 613-92-3 ]
N'-[(3-methylbut-2-enoyl)oxy]benzenecarboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 3-Methylbutenoic acid With chloroformic acid ethyl ester; triethylamine In 1,4-dioxane at 20℃; for 0.25h; Stage #2: N-hydroxybenzenecarboximidamide In 1,4-dioxane at 20℃; for 0.25h;	Synthesis and characterization of O-acylamidoximes 3a-p General procedure: Method A. An ethyl chloroformate (ECF, 3.0 mmol, 0.29 mL) was added, dropwise to a mixture of carboxylic acid (2.5 mmol) and TEA (3.0 mmol, 0.42 mL) in 1,4-dioxane (4 mL). The reaction mixture was stirred at room temperature for 15 min. An amidoxime 2 (2.5 mmol) in 1,4-dioxane (4 mL) was added and resulted mixture was stirred at room temperature for 15 min. The solvent was evaporated at reduced pressure and residue was diluted with water (25 mL). The precipitate was filtered off, washed with cold water (25 mL) and dried in air at room temperature.

Reference： [1]Tarasenko, Marina; Sidneva, Vera; Belova, Alexandra; Romanycheva, Anna; Sharonova, Tatyana; Baykov, Sergey; Shetnev, Anton; Kofanov, Eugeniy; Kuznetsov, Mikhail A. [Arkivoc, 2018, vol. 2018, # 7, p. 458 - 470]

71
[ 7345-82-6 ]
[ 613-92-3 ]
N'-[(2E)-3-(2,3-dimethoxyphenyl)prop-2-enoyl]oxy}benzenecarboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: trans-2,3-dimethoxycinnamic acid With chloroformic acid ethyl ester; triethylamine In 1,4-dioxane at 20℃; for 0.25h; Stage #2: N-hydroxybenzenecarboximidamide In 1,4-dioxane at 20℃; for 0.25h;	Synthesis and characterization of O-acylamidoximes 3a-p General procedure: Method A. An ethyl chloroformate (ECF, 3.0 mmol, 0.29 mL) was added, dropwise to a mixture of carboxylic acid (2.5 mmol) and TEA (3.0 mmol, 0.42 mL) in 1,4-dioxane (4 mL). The reaction mixture was stirred at room temperature for 15 min. An amidoxime 2 (2.5 mmol) in 1,4-dioxane (4 mL) was added and resulted mixture was stirred at room temperature for 15 min. The solvent was evaporated at reduced pressure and residue was diluted with water (25 mL). The precipitate was filtered off, washed with cold water (25 mL) and dried in air at room temperature.

Reference： [1]Tarasenko, Marina; Sidneva, Vera; Belova, Alexandra; Romanycheva, Anna; Sharonova, Tatyana; Baykov, Sergey; Shetnev, Anton; Kofanov, Eugeniy; Kuznetsov, Mikhail A. [Arkivoc, 2018, vol. 2018, # 7, p. 458 - 470]

72
[ 613-92-3 ]
[ 956-02-5 ]
(4-chlorophenyl)(2,4-diphenyl-1H-imidazol-5-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; 1,10-Phenanthroline; iodine; iron(II) chloride In chlorobenzene at 120℃; for 8h;	2. General procedure for the synthesis of (2,4-diphenyl-1H-imidazol-5-yl)(phenyl)methanone 3ab General procedure: The reactions were carried out in a round-bottom sidearm flask (10 mL). 1a (0.2 mmol), 2b (0.4 mmol), FeCl2 (10 mol%), 1,10-phen (10 mol%), I2 (60 mol%), DMAP (1 eq) and PhCl (1 mL) were added to the flask with magnetic stirring bar. The resulting mixture was stirred at 120 °C for 8 h. After cooling to room temperature, the mixture was filtered and extracted with ethyl acetate (3×10 mL). Then the filtrate was concentrated under reduced pressure in order to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 10/1 as eluent) to obtain product 3ab.

Reference： [1]Wu, Ping; Zhang, Xueguo; Chen, Baohua [Tetrahedron Letters, 2019, vol. 60, # 16, p. 1103 - 1107]

73
[ 613-92-3 ]
[ 956-02-5 ]
4-(4-chlorophenyl)-2,6-diphenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,10-Phenanthroline; iron(III) chloride hexahydrate; potassium carbonate In toluene at 120℃; for 10h;	2. General procedure for the synthesis of 2,4,6-triphenylpyrimidine 4ab General procedure: The reactions were carried out in a round-bottom sidearm flask (10 mL). 1a (0.2 mmol), 2b (0.4 mmol), FeCl3.6H2O (10 mol%), 1,10-phen (10 mol%), K2CO3 (2 eq) and Toluene (2 mL) were added to the flask with magnetic stirring bar. The resulting mixture was stirred at 120 °C for 10 h. After cooling to room temperature, the mixture was filtered and extracted with ethyl acetate (3×10 mL). Then the filtrate was concentrated under reduced pressure in order to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 50/1 as eluent) to obtain product 4ab.

Reference： [1]Wu, Ping; Zhang, Xueguo; Chen, Baohua [Tetrahedron Letters, 2019, vol. 60, # 16, p. 1103 - 1107]

74
[ 2403-27-2 ]
[ 613-92-3 ]
[ 58536-46-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1,10-Phenanthroline; iron(III) chloride hexahydrate; potassium carbonate; In toluene; at 120℃; for 10h;	General procedure: The reactions were carried out in a round-bottom sidearm flask (10 mL). 1a (0.2 mmol), 2b (0.4 mmol), FeCl3.6H2O (10 mol%), 1,10-phen (10 mol%), K2CO3 (2 eq) and Toluene (2 mL) were added to the flask with magnetic stirring bar. The resulting mixture was stirred at 120 C for 10 h. After cooling to room temperature, the mixture was filtered and extracted with ethyl acetate (3×10 mL). Then the filtrate was concentrated under reduced pressure in order to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 50/1 as eluent) to obtain product 4ab.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1103 - 1107

75
[ 956-04-7 ]
[ 613-92-3 ]
(4-(4-chlorophenyl)-2-phenyl-1H-imidazol-5-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; 1,10-Phenanthroline; iodine; iron(II) chloride In chlorobenzene at 120℃; for 8h;	2. General procedure for the synthesis of (2,4-diphenyl-1H-imidazol-5-yl)(phenyl)methanone 3ab General procedure: The reactions were carried out in a round-bottom sidearm flask (10 mL). 1a (0.2 mmol), 2b (0.4 mmol), FeCl2 (10 mol%), 1,10-phen (10 mol%), I2 (60 mol%), DMAP (1 eq) and PhCl (1 mL) were added to the flask with magnetic stirring bar. The resulting mixture was stirred at 120 °C for 8 h. After cooling to room temperature, the mixture was filtered and extracted with ethyl acetate (3×10 mL). Then the filtrate was concentrated under reduced pressure in order to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 10/1 as eluent) to obtain product 3ab.

Reference： [1]Wu, Ping; Zhang, Xueguo; Chen, Baohua [Tetrahedron Letters, 2019, vol. 60, # 16, p. 1103 - 1107]

76
[ 613-92-3 ]
[ 399-10-0 ]
(2,4-diphenyl-1H-imidazol-5-yl)(4-fluorophenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With dmap; 1,10-Phenanthroline; iodine; iron(II) chloride In chlorobenzene at 120℃; for 8h;	2. General procedure for the synthesis of (2,4-diphenyl-1H-imidazol-5-yl)(phenyl)methanone 3ab General procedure: The reactions were carried out in a round-bottom sidearm flask (10 mL). 1a (0.2 mmol), 2b (0.4 mmol), FeCl2 (10 mol%), 1,10-phen (10 mol%), I2 (60 mol%), DMAP (1 eq) and PhCl (1 mL) were added to the flask with magnetic stirring bar. The resulting mixture was stirred at 120 °C for 8 h. After cooling to room temperature, the mixture was filtered and extracted with ethyl acetate (3×10 mL). Then the filtrate was concentrated under reduced pressure in order to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 10/1 as eluent) to obtain product 3ab.

Reference： [1]Wu, Ping; Zhang, Xueguo; Chen, Baohua [Tetrahedron Letters, 2019, vol. 60, # 16, p. 1103 - 1107]

77
[ 37091-73-9 ]
[ 613-92-3 ]
1,3-dimethyl-2-(methyl(2-(methyl(3-phenyl-1,2,4-oxadiazol-5-yl)amino)ethyl)amino)-4,5-dihydro-1H-imidazol-3-ium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In dichloromethane; at 20℃; for 4h;	General procedure: 0.002 mol amidoximes and 0.008 mol triethylamine dissolved in 10 ml dichloromethane. The solution was then instilled to 10 ml dichloromethane containing 0.004 mol Vilsmeier salt and stirred for 4 h . The whole progress was monitored by TLC and evaporated the solvent then followed by column chromatography column chromatography to get terminated material.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 6959 - 6963

78
[ 1570-45-2 ]
[ 613-92-3 ]
[ 4969-62-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium hydroxide In dimethyl sulfoxide at 20℃; for 4h;	2.2 Synthesis and characterization of oxadiazoles (ODAs). General procedure 2 (GP2) General procedure: An amidoxime (30 mmol) and ester (36 mmol) was added to a suspension of powdered NaOH (36 mmol) in DMSO (10 mL). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with cold water (100 mL), and resulted precipitate was filtered off, washed with cold water (50 mL) and dried in air at room temperature. 3-Phenyl-5-(pyridin-4-yl)-1,2,4-oxadiazole (ODA-4, according to GP2): white solid; 4.62 g (69%) yield

Reference： [1]Geyl, Kirill; Baykov, Sergey; Tarasenko, Marina; Zelenkov, Lev E.; Matveevskaya, Vladislava; Boyarskiy, Vadim P. [Tetrahedron Letters, 2019, vol. 60, # 40]

79
[ 108-55-4 ]
[ 613-92-3 ]
sodium 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: glutaric anhydride,; N-hydroxybenzenecarboximidamide at 199.84℃; for 1h; Stage #2: With sodium hydroxide In methanol at 20℃; for 1h;	4.6. Synthesis of sodium 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate salts General procedure: In a round-bottom flask, the respective 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoic acid (0.8 mmol) and 3.2 mL of 1% NaOH methanol solution(freshly prepared) were mixed and the reaction was allowed tostir for one hour. After the time, methanol was evaporated and theproduct was recrystallized from chloroform.Sodium 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate (4a) (0.17 g,89%); mp 225-226 °C (from CHCl3); 1H NMR (D2O, 400 MHz, SiMe4)δ(ppm): 1.87 (q; 2H; J = 7.2 Hz, 7.6 Hz; CH2); 2.15 (t; 2H; J = 7.2 Hz;CH2); 2.75 (t; 2H; J = 7.6 Hz; CH2); 7.29-7.40 (m; 3H; Harom); 7.61(dd; 2H; J = 7.6 Hz, 1.6 Hz; Harom). 13C NMR (D2O, 100 MHz, SiMe4)δ(ppm): 25.3; 28.2; 39.2; 127.8; 129.6; 131.7; 134.3; 170.0; 183.4; 184.5. Elemental analysis for C12H11N2NaO3Calcd: C, 56.70; H, 4.36.Found: C, 55.93; H, 4.18.

Reference： [1]Guido, Rafael V. C.; Leal, Laylla L. L.; Maciel, Larissa G.; Oliveira, Andrew A.; Romão, Tatiany P.; Silva-Filha, Maria Helena N. L.; Soares, Thereza A.; dos Anjos, Janaína V. [Bioorganic and medicinal chemistry, 2020, vol. 28, # 2]

80
[ 73027-79-9 ]
[ 613-92-3 ]
C₁₃H₉Cl₂N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Step 1: To the stirred solution of compounds 5 and 7 (1.0 eq) in themixture of THF and water (2:1) was added lithium hydroxide monohydrate(2.2 eq), and the reaction mixture was stirred at room temperaturefor 4 h. The reaction mixture was concentrated under vacuo and diluted with water, acidified with an aqueous solution of citric acidup to pH-4 ~ 5. The compound was extracted with ethyl acetate, andthe combined organic layers were washed with brine, dried over anhyd.Na2SO4, filtered and concentrated under vacuo to afford acids 6 and 8. To the stirred solution of carboxylic acid (3 and 4) (1.0 eq) in DCM(10 mL/ mmol) was added carbonyldiimidazole (CDI) (1.1 eq) and thereaction mixture was stirred for 30 min. N-hydroxybenzamidine, 2(1.0 eq) was added to this mixture and was stirred at room temperaturefor 6 h. After completion, the reaction mixture was diluted with DCM,washed with water and brine, dried over anhyd. Na2SO4, filtered andconcentrated under vacuo. The crude product was dissolved in tolueneand refluxed for 16 h. After completion of the reaction (monitored byTLC), the reaction mixture was cooled, and the solvent was removedunder vacuo. The product was purified by column chromatographyeluted with ethyl acetate:hexane (2:8) to yield the pure product.

Reference： [1]Bioorganic Chemistry,2020,vol. 98

81
[ 29079-00-3 ]
[ 613-92-3 ]
[ 100087-43-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Sealed tube; regioselective reaction;	3.2. Typical Experimental Procedure for the Synthesis of 2,4-Diphenyl-1H-imidazole (3aa) General procedure: A mixture of benzamidoxime (1a, 136.1 mg, 1.0 mmol), phenylacetylene (2a, 204.1 mg, 2.0 mmol)and Cs2CO3 (815.1 mg, 2.5 mmol) in DMSO (4.0 mL), in a 25 mL screw-capped thick-walled Pyrextube was stirred at 100 °C for 24 h in an oil bath. After the reaction mixture was cooled to roomtemperature, it was poured into a solvent mixture of water (50.0 mL) and ethyl acetate (20.0 mL), andthe two phases were then separated. The aqueous layer was extracted with ethyl acetate (3 × 20.0 mL).The combined organic extracts were dried over anhydrous Na2SO4. After removal of the solventunder reduced pressure, the residue was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (gradient mixture ratio from 100:0 to 70:20) as eluent, to afford 3aa as awhite solid (160.4 mg, 73%).The characterization data for known products of 3aa, 3ab, 3af, 3ah-3al, 3an, 3ao, 3aq, 3ar, 3ba,3ca and 3da reported in the Supplementary Materials. Each of 3ac, 3ad, 3ae, 3ag, 3am, 3ap and 3edare new compounds, and their spectroscopic data are reported below.

Reference： [1]Hua, Ruimao; Iqbal, Muhammad Asif; Lu, Le; Mehmood, Hina [Molecules, 2020, vol. 25, # 16]

82
[ 2949-26-0 ]
[ 613-92-3 ]
4-(naphthalen-2-yl)-2-phenyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Sealed tube; regioselective reaction;	3.2. Typical Experimental Procedure for the Synthesis of 2,4-Diphenyl-1H-imidazole (3aa) General procedure: A mixture of benzamidoxime (1a, 136.1 mg, 1.0 mmol), phenylacetylene (2a, 204.1 mg, 2.0 mmol)and Cs2CO3 (815.1 mg, 2.5 mmol) in DMSO (4.0 mL), in a 25 mL screw-capped thick-walled Pyrextube was stirred at 100 °C for 24 h in an oil bath. After the reaction mixture was cooled to roomtemperature, it was poured into a solvent mixture of water (50.0 mL) and ethyl acetate (20.0 mL), andthe two phases were then separated. The aqueous layer was extracted with ethyl acetate (3 × 20.0 mL).The combined organic extracts were dried over anhydrous Na2SO4. After removal of the solventunder reduced pressure, the residue was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (gradient mixture ratio from 100:0 to 70:20) as eluent, to afford 3aa as awhite solid (160.4 mg, 73%).The characterization data for known products of 3aa, 3ab, 3af, 3ah-3al, 3an, 3ao, 3aq, 3ar, 3ba,3ca and 3da reported in the Supplementary Materials. Each of 3ac, 3ad, 3ae, 3ag, 3am, 3ap and 3edare new compounds, and their spectroscopic data are reported below.

Reference： [1]Hua, Ruimao; Iqbal, Muhammad Asif; Lu, Le; Mehmood, Hina [Molecules, 2020, vol. 25, # 16]

83
[ 501-65-5 ]
[ 613-92-3 ]
[ 484-47-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Sealed tube; regioselective reaction;	3.2. Typical Experimental Procedure for the Synthesis of 2,4-Diphenyl-1H-imidazole (3aa) General procedure: A mixture of benzamidoxime (1a, 136.1 mg, 1.0 mmol), phenylacetylene (2a, 204.1 mg, 2.0 mmol)and Cs2CO3 (815.1 mg, 2.5 mmol) in DMSO (4.0 mL), in a 25 mL screw-capped thick-walled Pyrextube was stirred at 100 °C for 24 h in an oil bath. After the reaction mixture was cooled to roomtemperature, it was poured into a solvent mixture of water (50.0 mL) and ethyl acetate (20.0 mL), andthe two phases were then separated. The aqueous layer was extracted with ethyl acetate (3 × 20.0 mL).The combined organic extracts were dried over anhydrous Na2SO4. After removal of the solventunder reduced pressure, the residue was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (gradient mixture ratio from 100:0 to 70:20) as eluent, to afford 3aa as awhite solid (160.4 mg, 73%).The characterization data for known products of 3aa, 3ab, 3af, 3ah-3al, 3an, 3ao, 3aq, 3ar, 3ba,3ca and 3da reported in the Supplementary Materials. Each of 3ac, 3ad, 3ae, 3ag, 3am, 3ap and 3edare new compounds, and their spectroscopic data are reported below.

Reference： [1]Hua, Ruimao; Iqbal, Muhammad Asif; Lu, Le; Mehmood, Hina [Molecules, 2020, vol. 25, # 16]

84
[ 613-92-3 ]
[ 1066-54-2 ]
[ 670-96-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Sealed tube; regioselective reaction;	3.2. Typical Experimental Procedure for the Synthesis of 2,4-Diphenyl-1H-imidazole (3aa) General procedure: A mixture of benzamidoxime (1a, 136.1 mg, 1.0 mmol), phenylacetylene (2a, 204.1 mg, 2.0 mmol)and Cs2CO3 (815.1 mg, 2.5 mmol) in DMSO (4.0 mL), in a 25 mL screw-capped thick-walled Pyrextube was stirred at 100 °C for 24 h in an oil bath. After the reaction mixture was cooled to roomtemperature, it was poured into a solvent mixture of water (50.0 mL) and ethyl acetate (20.0 mL), andthe two phases were then separated. The aqueous layer was extracted with ethyl acetate (3 × 20.0 mL).The combined organic extracts were dried over anhydrous Na2SO4. After removal of the solventunder reduced pressure, the residue was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (gradient mixture ratio from 100:0 to 70:20) as eluent, to afford 3aa as awhite solid (160.4 mg, 73%).The characterization data for known products of 3aa, 3ab, 3af, 3ah-3al, 3an, 3ao, 3aq, 3ar, 3ba,3ca and 3da reported in the Supplementary Materials. Each of 3ac, 3ad, 3ae, 3ag, 3am, 3ap and 3edare new compounds, and their spectroscopic data are reported below.

Reference： [1]Hua, Ruimao; Iqbal, Muhammad Asif; Lu, Le; Mehmood, Hina [Molecules, 2020, vol. 25, # 16]

85
[ 22110-53-8 ]
[ 613-92-3 ]
N-(adamantan-1-yl)-3-phenyl-1,2,4-oxadiazol-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In toluene at 20℃; for 4h;

Reference： [1]Fu, Jin-Ping; Pan, Ying-Ming; Tang, Hai-Tao; Teng, Qing-Hu; Wang, Xu; Xie, Jia-Xing [Organic and biomolecular chemistry, 2020, vol. 18, # 26, p. 4936 - 4940]

86
[ 21678-37-5 ]
[ 613-92-3 ]
[ 114065-31-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With Imidazole hydrochloride In neat (no solvent) at 100℃; for 6h;	2.2. General procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles 3a-3r, 4a-4d, 5a-5c and 6a-6c. General procedure: A round-bottom flask was charged with benzamidoxime 1a (0.5 g, 3.67 mmol, 1.0 equiv.), N,N-dimethylacetamide (1 ml, excess), and imidazole hydrochloride (2.5 equiv.). The mixture was stirred at 100 °C for 6 hours. Reaction was monitored by TLC. When the reaction reached completion, a saturated solution of NaCl (20 ml) was added. After extraction of aqueous phase with ethyl acetate (3×50 mL), the organic phase was dried over anhydrous Na2SO4 and concentrated in vacuum with silica gel added. The residue was separated by chromatography (petroleum ether/ethyl acetate 150:1) to obtain the desired product 3a.

Reference： [1]Wang, Xuetong; Wang, Yin; Liu, Xiaoling; He, Tingshu; Li, Lingli; Wu, Huili; Zhou, Shangjun; Li, Dan; Liao, Siwei; Xu, Ping; Huang, Xing; Yuan, Jianyong [Tetrahedron, 2021, vol. 100]

87
[ 53-86-1 ]
[ 613-92-3 ]
N'-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}benzenecarboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N-hydroxybenzenecarboximidamide In acetonitrile at 20℃; for 3h;	5.1. General procedure for the synthesis of N’-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}arylcarboximidamide (4a-g) General procedure: To a solution of indomethacin 1 (1.5 mmole, 0.53 g) in 30 ml acetonitrile, the N,N’-carbonyldiimidazole CDI (11 mmole, 1.2 g) was added and the mixture was stirred at room temperature for 30 mins. The respective amidoximes 3a-g (10 mmole) was then added and stirred for further 3 hrs. After completion of reaction (monitored with TLC), theformed precipitate was collected by filtration, washed several times with acetonitrile, dried and used without further purification to give 3a-g. 5.1.1. N’-{2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}benzenecarbox-imidamide (4a)Yield 85%; white solid; m.p.: 210-212 C. IR (ATR)) vmax 3491.63,3335.48 (NH2), 3063.77 (CH aromatic), 2992.64, 2928.61, 2832.96 (CHaliphatic), 1730.18 (C- -O), 1679.01 (C- -O benzoyl), 1608.82 (C- -N)cm 1; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 2.29 (s, 3H, CH3), 3.79 (s,3H, OCH3), 3.95 (s, 2H, CH2), 6.74 (d, J = 8.9 Hz, 1H, CHarom.), 6.85 (br.s, 2H, NH2), 6.94-6.97 (d, J = 8.9 Hz, 1H, CHarom.), 7.22 (s, 1H, CHarom.),7.43-7.51 (m, 3H, CHarom.), 7.65 (d, J = 7.7 Hz, 2H, CHarom.), 7.69-7.73(m, 4H, CHarom.); 13C NMR (100 MHz, DMSO-d6) δ (ppm): 13.68, 28.86,55.97, 102.48, 111.95, 113.43, 115.06, 127.21, 128.82, 129.54, 130.79,130.97, 131.13, 131.62, 132.01, 134.64, 135.94, 138.12, 156.14,157.46, 168.46, 168.71. Elemental Analysis Calcd. (%) forC26H22ClN3O4 (475.92): C, 65.62; H, 4.66; N, 8.83. Found: C, 65.52; H,4.54; N, 8.69.

Reference： [1]Mohamed, Mamdouh F.A.; Marzouk, Adel A.; Nafady, Ayman; El-Gamal, Dalia A.; Allam, Rasha M.; Abuo-Rahma, Gamal El-Din A.; El Subbagh, Hussein I.; Moustafa, Amr H. [Bioorganic Chemistry]

88
[ 53-86-1 ]
[ 613-92-3 ]
1-(4-chlorobenzoyl)-2-methyl-5-methoxy-3-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N-hydroxybenzenecarboximidamide In acetonitrile for 3h; Stage #3: In acetonitrile for 24h; Reflux;	5.2. General procedure for the synthesis of 1-(4-chlorobenzoyl)-2-methyl-5-methoxy-3-[(3-aryl-1,2,4-oxadiazol-5-yl)methyl]-1H-indole (5a-g) General procedure: To a solution of indomethacin 1 (1.5 mmole, 0.53 g) in 30 mlacetonitrile, the N,N’-carbonyldiimidazole CDI (11 mmole, 1.2 g) wasadded and the mixture was stirred at room temperature for 30 mins. Therespective amidoximes 3a-g (10 mmole) was then added and stirred for further 3 hrs. After that, the reaction mixture was heated at reflux for 24hrs (monitored with TLC) and cooled to room temperature. The formedprecipitate was collected by filtration, dried and recrystallized fromethanol to give compounds 5a-g. 5.2.1. 1-(4-Chlorobenzoyl)-2-methyl-5-methoxy-3-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]-1H-indole (5a)Yield 79%; pale beige solid; m.p.: 129-130 C. IR (ATR) vmax3080.82 (CH aromatic), 2983.91, 2925.47, 2839.92 (CH aliphatic),1687.68 (C- -O benzoyl), 1609.25 (C- -N) cm 1; 1H NMR (400 MHz,DMSO-d6) δ (ppm): 2.35 (s, 3H, CH3), 3.76 (s, 3H, OCH3), 4.56 (s, 2H,CH2), 6.75 (d, J = 8.4 Hz, 1H, CHarom.), 6.95 (d, J = 9.0 Hz, 1H, CHarom.),7.17 (s, 1H, CHarom.), 7.54-7.59 (m, 3H, CHarom.), 7.65 (d, J = 8.3 Hz,2H, CHarom.), 7.71 (d, J = 7.9 Hz, 2H, CHarom.), 7.98 (d, J = 7.6 Hz, 2H,CHarom.); 13CNMR (100 MHz, DMSO-d6) δ (ppm): 13.60, 21.86, 55.94,102.12, 112.12, 112.43, 115.19, 126.65, 127.45, 129.55, 129.70,130.46, 130.80, 131.71, 131.99, 134.44, 136.39, 138.27, 156.17,168.24, 168.39, 178.83. Elemental Analysis Calcd. (%) forC26H20ClN3O3 (457.90): C, 68.20; H, 4.40; N, 9.18. Found: C, 68.11; H,4.27; N, 9.09.

Reference： [1]Mohamed, Mamdouh F.A.; Marzouk, Adel A.; Nafady, Ayman; El-Gamal, Dalia A.; Allam, Rasha M.; Abuo-Rahma, Gamal El-Din A.; El Subbagh, Hussein I.; Moustafa, Amr H. [Bioorganic Chemistry]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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CAS No. :	613-92-3	MDL No. :	MFCD00031485
Formula :	C₇H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	136.15	Pubchem ID :	-
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	38.53
TPSA :	58.61 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

[ CAS No. 613-92-3 ] {[proInfo.proName]}

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[ 613-92-3 ]

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Log Po/w (iLOGP) :	1.16
Log Po/w (XLOGP3) :	1.05
Log Po/w (WLOGP) :	0.78
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	0.68
Consensus Log Po/w :	1.04

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.72
Solubility :	2.57 mg/ml ; 0.0189 mol/l
Class :	Very soluble
Log S (Ali) :	-1.87
Solubility :	1.83 mg/ml ; 0.0134 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.52
Solubility :	4.06 mg/ml ; 0.0299 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Signal Word:	Danger	Class:	9
Precautionary Statements:	P264-P270-P330-P301+P310-P405-P501	UN#:	3077
Hazard Statements:	H301-H410	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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Response
Code	Phrase
P301	IF SWALLOWED:
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P308	IF exposed or concerned:
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P370	In case of fire:
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P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
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P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 613-92-3 ] {[proInfo.proName]}

Quality Control of [ 613-92-3 ]

Related Doc. of [ 613-92-3 ]

Product Details of [ 613-92-3 ]

Calculated chemistry of [ 613-92-3 ]

Physicochemical Properties

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[ 613-92-3 ] Synthesis Path-Upstream 1~4

[ 613-92-3 ] Synthesis Path-Downstream 1~88

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Amidines

Precautionary Statements-General

Prevention

Response

Storage

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Inquiry

Related Functional Groups of
[ 613-92-3 ]