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CAS No. : | 7658-80-2 | MDL No. : | MFCD00014756 |
Formula : | C8H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KFXLXEQCRFGDRU-UHFFFAOYSA-N |
M.W : | 150.18 | Pubchem ID : | 82110 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 42.3 |
TPSA : | 55.12 Ų |
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) : | -7.06 cm/s |
Log Po/w (iLOGP) : | 1.37 |
Log Po/w (XLOGP3) : | 0.22 |
Log Po/w (WLOGP) : | 0.6 |
Log Po/w (MLOGP) : | 1.46 |
Log Po/w (SILICOS-IT) : | 0.65 |
Consensus Log Po/w : | 0.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.18 |
Solubility : | 9.89 mg/ml ; 0.0659 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.94 |
Solubility : | 17.4 mg/ml ; 0.116 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.41 |
Solubility : | 0.588 mg/ml ; 0.00392 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; at 20℃;Inert atmosphere; | General procedure: A mixture of corresponding hydrazine (1mmol), BrCN (1.2mmol), and EtOH (10 mL) was degassed with argon and stirred at room temperature overnight. The solvent was evaporated and the residue was purified by flash chromatography (DCM : MeOH = 20:1) to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate; In methanol; for 5h;Reflux; | General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C. | |
With hydrazine hydrate; In methanol; for 8h;Reflux; | General procedure: To a solution of methyl ester of aromatic carboxylic acid 2 (0.1 mol) in methanol (30 mL), hydrazine hydrate (0.2 mol) was added drop wise with stirring. The resulting mixture was allowed to reflux for 8 h. After the completion of the reaction as monitored by TLC, the excess methanol was distilled off under reduced pressure. The resulting acid hydrazide 3 was washed with cold water, dried and recrystallized from ethanol. | |
General procedure: A mixture of methyl benzoates (15.0 mmol), CH3OH (30.0 mL) wereplaced in a 100mL round-bottomed flask equipped with a magnetic stirrer.Stirring for 10 minutes in 0 C. Then hydrazine hydrate (4.0 eq.) was added to the flask. Afterword the mixture was stirred under reflux 8 h, the reaction system was concentrated to remove CH3OH and most of hydrazine hydrate. After cooling, the contents were added petroleum-ether (50 mL) by stirring, then the white solids would be separated, washed with water and dried under vacuum. The yield was 65%~80%. |
With hydrazine hydrate; In methanol; at 65℃; for 4h; | General procedure: To a solution of esters (2a~2t, 1.0 equiv.), furan-2-carbonyl chloride (7a, 1.0 equiv.) orthiophene-2-carbonyl chloride (7b, 1.0 equiv.) in MeOH (2 mL/1 mmol) was added hydrazine hydrate(1 mL/1 mmol), then the mixture was allowed to reach 65 C and stirred for 4 h. After completion(monitored by TLC), the organic solvent was removed and extracted three times with ethyl acetate,the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to givethe corresponding hydrazides (3a~3t, 8a, or 8b) in high yields, which were taken up for the next stepwithout any purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrazine hydrate; In ethanol; water;Reflux; | General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information). |
With hydrazine hydrate; In ethanol; for 24h;Reflux; | General procedure: Substituted aromatic acid (0.01 mol) was dissolved in 20 ml absolute ethanol added 1 ml conc. H2SO4 and refluxed for 8 h. The two third volume of reaction mixture was removed under reduced pressure and then poured into crushed ice and neutralized with sodium bicarbonate to obtain esters. In the subsequent step equimolar quantity of substituted ester (0.005 mol) and hydrazine hydrate (0.25 ml, 0.005 mol) in ethanol was refluxed for 24 h with stirring. The two third volume of alcohol was removed under reduced pressure and the reaction mixture was poured into the crushed ice. The resultant precipitate was filtered, washed with water and dried. The solid was recrystallized from 25 ml of 90 % ethanol. The purity of the compounds was checked by TLC using toluene-ethyl acetate-formic acid (5:4:1) as mobile phase. | |
With hydrazine hydrate; In ethanol;Reflux; | General procedure: Then, the corresponding ester was refluxed with 85% hydrazine monohydrate in ethanol to get hydrazide 1. |
With hydrazine hydrate; In ethanol; for 5h;Reflux; | General procedure: 5mL of hydrazine monohydrate (80%) was added to a solution of intermediate 3 (5mmol) in ethanol (5mL). The reaction mixture was maintained under reflux for 5h. was then concentrated under reduced pressure and the resulting solid was collected by filtration, washed with cold water and dried to give the desired intermediate 4 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol; for 22h;Reflux; | General procedure: A representative procedure for the synthesis of N'-[(9-ethyl-9H-carbazol-3-yl)methylene]-2-iodobenzohydrazide (NP-10) is as follows: Tothe flask was added 2-iodobenzohydrazide (655 mg, 2.50 mmol),N-ethylcarbazole-3-carboxaldehyde (838 mg, 3.75 mmol, 1.50 equiv) and ethanol (20 mL),and the mixture was stirred at reflux temperature for 22 h. The resulting solid was filtered,washed with ethanol, and dried under vacuum to giveN'-[(9-ethyl-9H-carbazol-3-yl)methylene]-2-iodobenzohydrazide (NP-10) as a white solid(1.04 g, 89% yield). Other derivatives were synthesized in a similar manner, using anappropriate benzohydrazide as the starting material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃;Reflux; | General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium hydroxide; In acetonitrile; at 10℃; | To a solution of compound 2 (2.3g, 15.3mmol) in acetonitrile was added simultaneously compound 3 (1.73g, 15.3mmol) and 50% sodium hydroxide (0.61g, 15.3mmol) while maintaining the internal temperature below 100C. After 30mins, the mixture was extracted with EA and then the EA layer was concentrated to give Compound 4 as a white solid (2.3g). Yield: 66%. |
With sodium hydroxide; In acetonitrile; at 0℃; for 1h; | General procedure: To the slurry of benzoylhydrazide (1 equiv) in acetonitrile (20 mL)were added simultaneously choroacetylchloride (1.2 equiv) and 50%sodium hydroxide (1.2 equiv) while maintaining temperature below 0C. After 1 h, the resulting slurry was filtered and the solid was washedwith water (2×5 mL). The filter cake was dried to provide the intermediates5a-e as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Then equimolar portions of the appropriately substituted benzoylhydrazine (5 mmol) and potassium hydroxide (5 mmol) were dissolved in 20 mL of 95% ethanol. The mixture was allowed to stir for several minutes at room temperature and then carbon disulfide (7.5 mmol) was slowly added dropwise to the reaction system via a self-equalizing addition funnel while the mixture was heated to reflux. After 24 h, the solvent was completely removed under reduced pressure. The residue obtained was dissolved in water (50 mL) and diluted hydrochloric acid was added to adjust the pH values of the solution to 5-6. Then the precipitate was collected by filtering under reduced pressure, washed with water for several times and dried without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The hydrazide 1 was stirred with KOH in absolute methanol and carbon disulfide (CS2) was slowly added. The mixture was stirred 24h at room temperature and the white solid was precipitated, dried. The solid was refluxed with 85% hydrazine monohydrate to obtain the intermediate 2. The crude product was purified by silica gel column chromatography DCM/methanol (40:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With acetic acid; In ethanol; at 20℃; for 6h; | General procedure: to a mixture solution of 3-formylchromone d1 (174 mg, 1 mmol) and benzohydrazide e1 (136 mg, 1 mmol) in 25 mL ethanol was added three drops of acetic acid with stirring for 6 h at room temperature. Insoluble solid was gradually generated, then filtered and washed several times with ethanol. After drying, pure target compound f1 was afforded (227 mg, yield 78%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.6% | With trichlorophosphate; at 105 - 110℃; | General procedure: An equimolar mixture of N-carboxyl-2-(4-oxo-2-thioxothiazolidin-3-yl) 1 with the appropriate benzohydrazide 2 was refluxed with phosphorous oxychloride (105-110C) for 5-7h. Reaction mixture was quenched with ice water and the solid separated was filtered off, washed with water and further purified by silica gel column chromatography (dichloromethane/petroleum ether, 80:1) to afford yellow or reddish brown compounds 3a-k and 5a-c. The yield, melting point and spectral data of each compound are given below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With hydrazine; at 250℃;Microwave irradiation; | General procedure: N4-amino 1,2,4-triazoles were obtained directly in excellentyields from the reaction of substituted aryl acids (0.010 mol) withexcess of hydrazine hydrate (0.08 mol) in absence of organic solvents under microwave irradiation (800 W, 250 C) for 4-12 min.The products obtained were recrystallized from alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.5% | With trichlorophosphate; at 20℃; for 3h;Reflux; | General procedure: To a mixture of (0.31 g, 1.24 mmol) of 3,5-di-tert-butyl-4-hydroxybenzoic acid and 1.24 mmolearyl acid hydrazide in a 50 mL round bottom flask, 5 mL of phosphorus oxychloride was added in a fewportions at room temperature. The mixture was refluxed for 3 h with stirring on water bath 80-90 C.After cooling, the mixture poured onto 100 mL crushed ice and stirred for 15 min. Sodium bicarbonatewas added in a few portions until the pH was around to 7-8. The precipitate was filtered, washed withwater and dried then purified either by column chromatography or by crystallization from suitable solvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With trichlorophosphate; for 6h;Reflux; | General procedure: A mixture of aryl acid hydrazide (10mmol), chloroacetic acid (10mmol) and POCl3 (7mL) was heated under reflux for 6h. The excess POCl3 was removed under reduced pressure and the residue was poured onto crushed ice. The resuting precipitate was filtered, washed with saturated sodium bicarbonate solution and then with water, dried and recrystallized from ethanol/water to afford compound 7. |
With trichlorophosphate; In N,N-dimethyl-formamide; at 105 - 110℃; | General procedure: An equimolar mixture of chloroacetic acid and an appropriate benzohydrazide was refluxed in phosphorus oxychloride (105-110C) for 5-6 h. The resulting mixture was cooled to room temperature and poured into ice water to give a solid, which was filtered and washed several times with cold water. The solid was dried and then purified by silica gel column chromatography eluting with a 20:1 (v/v) mixture of dichloromethane and petroleum ether to yield the products 4a-k (70-80%) as white solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In methanol; | H2L1and H2L2were prepared by the same method.3-Bromosalicylaldehyde (0.01 mol, 2.01 g) reacted with <strong>[7658-80-2]2-methylbenzohydrazide</strong> (0.01 mol, 1.50 g) and 2-methoxybenzohydrazide (0.01 mol, 1.66 g), respectively, in methanol,affording H2L1and H2L2,respectively.H2L1: Yield: 87%. IR (cm1, KBr) nmax3447w, 3311m,1660s, 1603 m, 1511s, 1473s, 1395w, 1343w, 1286m, 1233s,1176w, 1137 m, 1008w, 936w, 795w, 750 m, 666w, 517 m.Anal. Calcd. for C15H13BrN2O3: C, 51.6; H, 3.8; N, 8.0%.Found: C, 51.5; H, 3.6; N, 8.1%.1H NMR (300 MHz,d6-DMSO)d 12.58 (s, 1H), 11.91 (s, 1H), 7.69 (dd, JD7.6,1.7 Hz, 1H), 7.63 (dd, JD7.9, 1.3 Hz, 1H), 7.6-7.5 (m, 1H),7.47 (dd, JD7.7, 1.4 Hz, 1H), 7.20 (d, 1H), 7.10 (t, 1H), 6.90(t, 1H), 3.90 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In butan-1-ol; at 150℃; | General procedure: The triazoles of escitalopram (60-88) were synthesized byfollowing a reported method for triazole formation.25 A mixtureof a benzohydrazide (33 mmol), escitalopram (59-oxalate,10 mmol) and K2CO3 (0.5 mmol) in n-butanol (2 mL) was heatedat 150 C for 5-6 h. The reaction was monitored with TLC. Afterthe completion of the reaction, the solvent was removed underreduced pressure. Finally, the triazole derivatives of escitalopram(60-88) were purified with column chromatography using solventsystem CH3OH/CH3Cl = 60:40 and finally with preparative thinlayer chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In methanol; at 20℃; for 0.5h; | 5-Methylsalicylaldehyde (1.0 mmol,0.14 g) and <strong>[7658-80-2]2-methylbenzohydrazide</strong> (1.0 mmol, 0.15 g) were dissolved in methanol (30 mL) with stirring. The mixture was stirred for about 30 min at room temperature to give colorless solution. The solution was left still in air to slow evaporate of most of the solvent, to give crystalline product of H2L. The product was isolated by filtration and washed with cold methanol. The yield was 87%. Selected IR data (KBr; nu, cm-1): 3237 (N-H), 1641(C=O), 1616 (C=N). For C16H16N2O2 anal. calcd., %: C, 71.62; H, 6.01; N, 10.44. Found, %: C, 71.53; H, 6.12; N, 10.55. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.9% | In ethanol; at 4℃; for 24h; | The benzaldehyde (1 mmol, 2 ml ethanol) and the benzohydrazide (1 mmol in2 ml hot ethanol) were combined. All products - except 3 and 7 - crystallized within seconds. After 30 minutes at room temperature theproduct was collected by filtration (Yield: 80 to 95%) . Homogeneity of the product was confirmed by thin layer chromatography (TLC) on silicagel F254 (Merck KGaA, Darmstadt, Germany) in two different solvent systems benzene / acetic acid 9:1 v/v and hexane / ethylacetate 1:3 v/v. If impurities were present the product was recrystallized from ethanol. For the synthesis ofcompounds 3 and 7 the reaction was conducted as described above. After 24h at 4 C the solvent was completely evaporated and the product crystallized from ethylacetate (Yields: 3 = 72.9%, 7 = 67.3%) . Products were analyzed by TLC as described above. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h; | 7-[l-(te^butoxycarbonyl)piperidin-4-yl]-5-oxo-4,5-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid (150 mg, 0.42 mmol) and 2-methyibenzohydrazide (93 mg, 0.6 mmol) were dissolved in N,N- Dimethylformamide (1,5 ml). N,N-Diisopropylethylamin (0.22 ml, 1.24 mmol) and N- [(Dimethylamino)(3H-[l,2,3]triazolo[4,5-b]pyridin-3-yloxy)methyliden]-N-methyl-methanaminium- hexafluorophosphate (266 mg, 0.62 mmol) were added and the mixture was stirred for 16h at RT. The mixture was purified via reverse phase HPLC (gradient acetonitrile/water with 0.01 % triiluoroacetic acid) which afforded the title compound (117 mg, 56% of theory). LC-MS (Method 5B): Rt = 0.85 min, MS (ESIPos): m z = 495.4 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 24h;Sealed tube; Irradiation; | General procedure: A sealed tube equipped with a magnetic stir bar was charged with acylhydrazine 1 (0.5 mmol), alpha-keto acid 2 (0.5 mmol), K2CO3 (1 mmol), PANI-g-C3N4-TiO2 (40 mg) and DMF (5.0 mL). The mixture was then irradiated with a 14 W CFL and stirred at room temperature (25 C) for 24 h. The distance of the reaction vial from the light is about 5 centimeters. After reaction, the mixture was diluted with EtOAc (10 mL) and H2O (5 mL), and the solid catalyst was recovered by centrifugation. The aqueous phase was extracted with EtOAc (5 mL × 3). The collected organic extracts were dried on Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography on silica gel using a mixture of PE/EA (20:1) to give the pure product 3. |
59% | With tert.-butylhydroperoxide; sodium carbonate; potassium iodide; In 1,4-dioxane; at 120℃; for 5h;Sealed tube; | General procedure: In a 35 mL sealed tube, a solution of 3 mL of 1,4-dioxane, acyhydrazines 1 (0.5mmol), alpha-ketoacids 2 (0.5 mmol) , Na2CO3 (0.6 mmol), KI (0.05 mmol) and TBHP (2.0 mmol) was sequentially added. The reaction mixture was stirred at 120 C for 5 h and then cooled to room temperature. Then, the mixture extracted with ethyl acetate (2 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 (PE:EA = 20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tert.-butylhydroperoxide; iron(III) chloride; In acetonitrile; at 80℃; | Using <strong>[7658-80-2]2-methylbenzohydrazide</strong> and aniline as raw material, the reaction steps are as follows: In the reaction flask was added 0.075 g (0.5 mmol) of <strong>[7658-80-2]2-methylbenzohydrazide</strong>, aniline 0.0465 g (0.5 mmol), 0.0081 g (0.05 mmol) of iron trichloride, tert-butyl hydroperoxide (0.3 mL, 3 mmol) and 5 mL of acetonitrile at 80 C; TLC followed the reaction until complete; The crude product obtained after the end of the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the object product (yield 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In 1-methyl-pyrrolidin-2-one; for 20h;Inert atmosphere; Cooling with ice; | Step 1 : Synthesis of N-3-bromobenzoyl-N'-2-methylbenzoylhydrazide Into a 500 mL three-neck flask were put 25 g (166 mmol) of o-toluic hydrazide and 120 mL of N-methyl-2-pyrrolidinone ( MP). The atmosphere in the flask was replaced with nitrogen, and the mixture was stirred while being cooled with ice. To this mixed solution, a mixed solution of 37 g (166 mmol) of 3-bromobenzoyl chloride and 50 mL of NMP was slowly added dropwise, and the mixture was stirred for 20 hours to be reacted. After the reaction, the reacted solution was slowly added to 300 mL of water, so that a solid was precipitated. The precipitated solid was subjected to ultrasonic cleaning in which water and 1M hydrochloric acid were used alternately. Then, ultrasonic cleaning of the solid was performed using ethanol, whereby 40 g of a white solid was obtained in a yield of 71 %. The obtained white solid was identified as N-3-bromobenzoyl-A^-2-methylbenzoylhydrazide by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-5) below. |
71% | With hydrogenchloride; In 1-methyl-pyrrolidin-2-one; for 20h;Inert atmosphere; Cooling with ice; | 25.0 g (166 mmol) of o-toluyl hydrazide and 120 mL of N-methyl-2-pyrrolidinone (NMP) were added to a 500-mL three-neck flask. The atmosphere in the flask was replaced with nitrogen. Then, the mixture was stirred while being cooled with ice. To this mixed solution, a mixed solution of 36.5 g (166 mmol) of 3-bromobenzoyl chloride and 50 mL of NMP was slowly added dropwise, and the mixture was stirred for 20 hours. After reaction for the predetermined time, this reacted solution was slowly added to 300 mL of water, so that a white solid was precipitated. The precipitated solid was subjected to ultrasonic cleaning in which water and 1M hydrochloric acid were used alternately. After that, ultrasonic cleaning using ethanol was performed, so that 39.5 g of a white solid was obtained in a yield of 71%. By a nuclear magnetic resonance (NMR) method, the obtained white solid was identified as N-3-bromobenzoyl-N?-2-methylbenzoylhydrazide. The synthesis scheme of Step 1 is shown in (a-0). |
71% | In 1-methyl-pyrrolidin-2-one; for 20h;Inert atmosphere; | Into a 500 mL three-neck flask were put 25 g (166 mmol) of o-toluic hydrazide and 120 mL of N-methyl-2-pyrrolidinone (NMP). The atmosphere in the flask was replaced with nitrogen, and the mixture was stirred while being cooled with ice. To this mixed solution, a mixed solution of 37 g (166 mmol) of 3-bromobenzoyl chloride and 50 mL of NMP was slowly added dropwise, and the mixture was stirred for 20 hours to be reacted. After the reaction, the reacted solution was slowly added to 300 mL of water, so that a solid was precipitated. The precipitated solid was subjected to ultrasonic cleaning in which water and 1M hydrochloric acid were used alternately. Then, ultrasonic cleaning of the solid was performed using ethanol, whereby 40 g of a white solid was obtained in a yield of 71%. The obtained white solid was identified as N-3-bromobenzoyl-N'-2-methylbenzoylhydrazide by nuclear magnetic resonance (NMR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-5) below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.9% | In 1-methyl-pyrrolidin-2-one for 43h; Inert atmosphere; | 1.1 Step 1: Synthesis of N-3-pentafluorosulfanylbenzoyl-N-2-methylbenzoylhydrazide Into a 100-mL three-neck flask were put 5.6 g (37.3 mmol) of o-toluyl hydrazide and 25 mL of N-methyl-2-pyrrolidinone (NMP), and the mixture was stirred under a nitrogen stream. To this mixed solution was slowly added a solution in which 10 g (37.5 mmol) of 3-(pentafluorosulfanyl)benzoyl chloride and 5 mL of NMP are mixed, and stirring was performed for 43 hours. After reaction for the predetermined time, the reacted solution was added to 200 mL of water, so that a white solid was precipitated. The precipitated white solid was washed in such a manner that ultrasonic cleaning using water and ultrasonic cleaning using 1M hydrochloric acid were alternately performed twice (four times in total). Then, a light brown solid was collected. The light brown solid was recrystallized with ethanol to give 9.2 g of a light brown solid in a yield of 64.9%. The obtained light brown solid was identified as N-3-pentafluorosulfanylbenzoyl-N-2-methylbenzoylhydrazide by nuclear magnetic resonance (NMR) spectroscopy. The synthesis scheme of Step 1 is shown in Synthesis Scheme (A-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | General procedure: 5-(Aroylhydrazinocarbonyl)escitalopram (58-84) were synthesized by the coupling reaction conditions mostly used in peptide synthesis [19]. 5-Carboxyescitalopram (3, 0.001mmol) and benzohydrazide (31, 0.001mmol) were dissolved in DMF (15mL). After five minutes stirring, HBTU (0.0012mmol) was incorporated and stirred for 20min. Then DIEA (0.002mmol) was added and stirred for 1h. Saturated solution of NH4Cl (1×10mL) was added into the reaction mixture and extracted with ethyl acetate (3×10mL). The ethyl acetate layer was washed with solution of NaHCO3 (5%, 2×10mL) followed by brine (1×10mL) and dried over anhydrous MgSO4 overnight. After the removal of ethyl acetate under reduced pressure, the residue was purified using column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With acetic acid; In ethanol; for 3h; | General procedure: Appropriate substituted benzoyl hydrazine 4 (1 equiv) was added to a solution of intermediate 2 (1mmol) in ethanol (10mL). The reaction mixture was stirred for 3h at reflux under the condition of the presence of acetic acid as catalyzer, then poured into cold water and the resulting solid was collected by filtrated, washed with EtOH (10mL), and dried in the atmospheric pressure to give the desired title compounds A, B, and C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With acetic acid; In ethanol; for 3h; | General procedure: Appropriate substituted benzoyl hydrazine 4 (1 equiv) was added to a solution of intermediate 2 (1mmol) in ethanol (10mL). The reaction mixture was stirred for 3h at reflux under the condition of the presence of acetic acid as catalyzer, then poured into cold water and the resulting solid was collected by filtrated, washed with EtOH (10mL), and dried in the atmospheric pressure to give the desired title compounds A, B, and C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With cerium(III) chloride heptahydrate; In ethanol; at 65℃; | General procedure: To a stirred suspension of alpha-oxopropane-4-nitrophenylhydrazone(5) (0.48 mmol) and the appropriate hydrazide (0.48 mmol)in 4.0 mL of ethanol, cerium (III) chloride heptahydrate (10 mol%)was added and the reaction mixture was stirred at 65 C during 1-3 h. Reaction?s completion was monitored by TLC, using appropriate eluent system. Once concluded, the heating was put away, and the reaction mixture was allowed to reach room temperature, giving yellow to orange precipitates. After cooling, the solids were filtered off under vacuum, and washed with cold ethanol. 1H NMR analysis of all products confirmed their purity. Recrystallization from ethanol afforded the samples for biological purposes, which were dried in an Abderhalden?s apparatus to remove traces of solvent. Yields, melting points, spectroscopic and spectrometric data are listed below for each new compound |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | General procedure: Trifluoromethyl ketones (1; 0.30 mmol, 1 equiv), acylhydrazines (2; 0.45 mmol, 1.5 equiv) and TsOH (20 mol%) were added to a dried round-bottom flask (50 mL) fitted with a magnetic bar. 1,4-Dioxane 4 mL) was then added and the mixture was stirred and heated to reflux. After the formation of acylhydrazones (monitored by TLC), tin powder (1.35 mmol, 4.5 equiv) and ethyl 2-(bromomethyl)acrylate (3; 1.20 mmol, 4 equiv) were added to the flask. When acylhydrazones had essentially disappeared (monitored by TLC), the reaction mixture was cooled to r.t., then 1,4-dioxane was removed under vacuum. Saturated NH4Cl solution (10 mL) was added and the mixture was stirred for 10 min. The mixture was extracted with EtOAc (3 × 10 mL) and the combined organic phases were dried (MgSO4) and concentrated. Purification of the residue by silica gel column chromatography (petroleum ether-EtOAc, 4:1) furnished the pure products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: A mixture containing acetyl acetone, 3-chloro-2,4-pentanedione, 3-aryloxy-2,4-pentanediones and ethyl acetoacetate was ground in the presence of piperidine as a catalyst. The reaction was carried out in a glass mortar and pestle at room temperature. After grinding for 5-10min, hydrazine hydrate or suitable aryl hydrazines (1mmol) was added, and the grinding was continued for further 10min. The progress of the reaction was monitored by TLC using n-hexane/ethyl acetate (8:2). On completion, the reaction mixture was diluted with ethyl acetate and filtered to remove salts, and the filtrate was concentrated. Recrystallization from ethanol afforded pure products (3a-3o), (4a-c) [38] and (5a-b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In ethanol; at 80℃; | General procedure: An equimolar mixture of 7-hydroxy-4-methyl-2H-chromen-2-one (3) (0.0025 mol; 0.44 g) and substituted arylhydrazide analogues (4e-j) (0.0025 mol) was suspended in20 mL ethanol and the reaction mixture was heated and refluxed at 80C for 4 h. The reaction was monitored on preparatory thin layer chromatography (TLC) using solvent system benzene/acetone (8:2). The reaction mixture was concentrated in vacuum and dipped into crushed ice to obtain the creamy solid precipitate. The solid was filtered,washed with water and dried to obtain substituted-N-(7-hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)benzamide (5e-i)and N-(7-hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)thiophene-2-carboxamide (5j). The substituted aryl/ heteroaryl hydrazideanalogues (4e-j) were prepared as per the reported method[20]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With acetic acid; In methanol; at 20℃; | To a solution of <strong>[7658-80-2]2-methylbenzoic hydrazide</strong> (0.66 mmol), 2-hydroxy-5- bromobenzaldehyde (0.72 mmol) in methanol (3 mL) was added 3 drops of glacial acetic acid. The reaction mixture was stirred at room temperature overnight. Addition of water to the reaction mixture resulted in precipitation of the product, which was filtered, washed with water and dried to give pure product as white solid. (95 % yield);1H NMR (500 MHz, DMSO-d6) delta 2.38 (s, 3 H), 6.90 (d, 1 H, J = 8.8 Hz), 7.28 - 7.32 (m, 3 H), 7.37 - 7.43 (m, 2 H), 7.47 (d, 1 H, J = 7.5 Hz), 7.78 (s, 1 H), 8.47 (s, 1 H), 11.19 (s, 1 H), 12.05 (s, 1 H). |
78% | In methanol; for 0.5h;Reflux; | A methanolic solution (20 mL) containing 5-bromo-2-hydroxybenzaldehyde (1.0 mmol, 0.201 g)was added dropwise to a methanolic solution of <strong>[7658-80-2]2-methylbenzohydrazide</strong> (1.0 mmol, 0.148 g) with constant stirring. Themixture was refluxed for 30 min, and the resulting precipitate was filtered off, washed with cold methanol, and dried ina desiccator over silica gel.Yield: 0.26 g, 78%. FT-IR (KBr), cm-1: nu(OH) 3447, nu(NH) 3231, nu(CH) 2810-3130, nu(C=O) 1647, nu(C=N) 1607,nu(C-O) 1252. 1H NMR (300 MHz, DMSO-d6, ppm): delta = 12.15 (s, 1H, OH), 11.21 (s, 1H, NH), 8.59 (s, 1H, CH=N), 7.92(d, 1H, ArH), 7.78 (s, 1H, ArH), 7.61 (t, 1H, ArH), 7.43 (d, 1H, ArH), 7.31 (d, 1H, ArH), 7.21 (t, 1H, ArH), 6.90 (d, 1H,ArH), 2.45 (s, 3H, CH3). Anal. calcd. (%) for C15H13BrN2O2: C 54.07, H 3.93, N 8.41. Found (%): C 53.85, H 4.02, N 8.33. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With dipotassium peroxodisulfate; copper(l) iodide; at 120℃;Green chemistry; | In a 25 mL tube, 0.2 mmol of <strong>[7658-80-2]2-methylbenzoic acid hydrazide</strong>, 0.05 mmol of cuprous iodide, and 0.2 mmol of potassium persulfate were added.Adding DMF (N,N-dimethylformamide) as a solvent,Stir at 120 C. After TLC (thin layer chromatography) detection, the reaction solution was cooled to room temperature.The reaction solution is filtered,extraction,The filtrate is evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography.The target product 2-(2-tolyl)-1,3,4-oxadiazole is obtained.The column chromatography eluent used was in a volume ratio of 3:1 petroleum ether: ethyl acetate mixture,The yield was 62%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.35% | General procedure: Add in a 100ml reaction flask at 0 CN-(2-formic acid phenyl)uracil-5-sulfonamide(2.50g, 8.07mmol) dissolved in 20ml of DMF, addedHOBT (1.25 g, 9.68 mmol) and EDCI (1.75 g, 9.68 mmol),After reacting for 1 hour, the reaction was continued at room temperature for 2 h, and phenylhydrazine hydrochloride was added.(1.25 g, 9.68 mmol); after the reaction is completed, the reaction solution is slowly poured into water.Precipitate the solid, adjust the pH of the solution to 2-3 with 10% dilute hydrochloric acid, and filter to obtain a solid.Wash with saturated Na2CO3 solution to obtain a light brown solid powder.The target compound was dried to 2.40 g, yield: 74.45%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.35% | General procedure: At 0 C, atAdd N-(3-formic acid phenyl)uracil-5-sulfonamide to 100 ml reaction flask(2.50 g, 8.07 mmol) was dissolved in 20 ml of DMF and added to HOBT (1.25 g, 9.68 mmol)And EDCI (1.75g, 9.68mmol), after 1 hour of reaction, continue to react at room temperature2h, phenylhydrazine hydrochloride (1.25g, 9.68mmol) was added;After the reaction is completed, the reaction solution is slowly poured into water to precipitate a solid.Adjust the pH of the solution to 2-3 with 10% dilute hydrochloric acid, and filter to obtain a solid.Washing with a saturated Na2CO3 solution gave a white solid powder. The target compound was dried to 2.45 g, yield: 76.00%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | The specific steps are as follows: adding 0.6 mmol of 2-methylquinoline, 0.9 mmol of elemental iodine, and 2 mL of dimethyl sulfoxide to a 15 mL pressure-resistant tube, and magnetically stirring the reaction at 110 C for 4 hours. After the reaction is cooled, 0.5 mmol is added. 2-methyl-benzohydrazide and 3 mmol of potassium carbonate were magnetically stirred at 110 C for 6 hours. After the reaction was completed, the reaction solution was extracted, and the organic layer was washed and dried.Dry and vacuum distillation to remove the solvent to obtain the crude product. The crude product is purified by column with petroleum ether/ethyl acetate=5:1 (V/V) as the eluent to obtain the desired product. The product is yellow solid. The rate is 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; at 80℃; for 6h; | General procedure: To a solution of hydrazides (3a~3t, 8a, or 8b, 1.0 equiv.) 10% NaOH aqueous solution(1.5 mL/1 mmol) was added ammonium thiocyanate (3.0 equiv.), then the mixture was heatedto 80 C and stirred for 6 h. The mixture was then cooled to room temperature and filtered. The filtratewas neutralized to pH 3-4 by concentrated hydrochloric acid, and the resulting white solid was collectedby filtration. The combined filter cake was dried to give the 2,4-dihydro-3H-1,2,4-triazole-3-thiones in72%-83% yields. |
Tags: 7658-80-2 synthesis path| 7658-80-2 SDS| 7658-80-2 COA| 7658-80-2 purity| 7658-80-2 application| 7658-80-2 NMR| 7658-80-2 COA| 7658-80-2 structure
[ 154660-48-7 ]
[1,1'-Biphenyl]-2-carbohydrazide
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[ 154660-48-7 ]
[1,1'-Biphenyl]-2-carbohydrazide
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[ 154660-48-7 ]
[1,1'-Biphenyl]-2-carbohydrazide
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[ 154660-48-7 ]
[1,1'-Biphenyl]-2-carbohydrazide
Similarity: 0.92
[ 154660-48-7 ]
[1,1'-Biphenyl]-2-carbohydrazide
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