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CAS No. : | 497-18-7 | MDL No. : | MFCD00007591 |
Formula : | CH6N4O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XEVRDFDBXJMZFG-UHFFFAOYSA-N |
M.W : | 90.08 | Pubchem ID : | 73948 |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 18.53 |
TPSA : | 93.17 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.96 cm/s |
Log Po/w (iLOGP) : | -0.08 |
Log Po/w (XLOGP3) : | -1.57 |
Log Po/w (WLOGP) : | -1.97 |
Log Po/w (MLOGP) : | -1.66 |
Log Po/w (SILICOS-IT) : | -1.37 |
Consensus Log Po/w : | -1.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.72 |
Solubility : | 476.0 mg/ml ; 5.28 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.12 |
Solubility : | 119.0 mg/ml ; 1.32 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.88 |
Solubility : | 688.0 mg/ml ; 7.64 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.63 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 | UN#: | 3077 |
Hazard Statements: | H302-H319-H372-H410 | Packing Group: | Ⅲ |
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 |
---|---|---|
With hydrogenchloride; In water; at 20℃; for 2h; | General procedure: Carbohydrazones 1-7 were prepared by reactions of <strong>[497-18-7]carbohydrazide</strong> (1,3-diaminourea,10 mmol) and appropriate aldehydes and ketones (5 mmol) in water (10 ml) at room temperaturewith addition one drop of conc. hydrochloric acid. Reaction mixture was stirred for 2h and the resulting precipitate was collected by filtration, and recrystallized from a suitablesolvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol; water; for 1h;Reflux; | 1,5-Bis(2-hydroxybenzaldehyde)carbohydrazone (H4L) wasprepared by a slight modification of the procedure reported previously [23]. Briefly, a mixture of 2-hydroxybenzaldehyde (1.1 ml, 10.0 mmol) in ethanol (20 mL) and <strong>[497-18-7]carbohydrazide</strong> (0.45 g, 5.0 mmol) in water/ethanol 1:2 (20 ml) was refluxed for 1 h. The white solid formed was filtered off, washed with ethanol (5 ml), diethyl ether (5 ml) and dried in air. Yield: 1.42 g (90%). Anal. Calc. for C15H14N4O3H2O: C, 56.96; H, 5.10; N, 17.71. Found: C, 56.83; H,5.02; N, 18.16%. 1,5-Bis(2-hydroxybenzaldehyde)thiocarbohydrazone (H4LS) was synthesised by following a literature protocol [22]. |
With hydrogenchloride; In ethanol; water; for 3h;Reflux; | General procedure: Components 8-14 were prepared by condesation of <strong>[497-18-7]carbohydrazide</strong> (10 mmol) in ethanol(40 ml) and appropriate aldehydes or ketones (21 mmol) dissolved in ethanol (10 ml) underreflux for 3 h with addition of one drop of conc. hydrochloric acid. After completion ofreaction, the resulting precipitate was collected by filtration and washed successively withcold alcohol, ethyl ether, dried and recrystallized from a suitable solvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With acetic acid; In ethanol; for 4h;Reflux; | The ligand was synthesized by refluxing 2-acetylpyridine (0.30 ml, 2.7 mmol) and <strong>[497-18-7]carbohydrazide</strong> (0.10 g, 1.1 mmol) in 2:1 M ratio in hot ethanol with adding few drops of glacial acetic acid to the reaction mixture [7]. The solution was heated for 4 h and on cooling a white solid was precipitated. The product was recrystallized from absolute ethanol as colorless needles, Yield 80%. The compound was checked by its m.p., (decomp. at 186 C), IR and 1H NMR spectra. |
With hydrogenchloride; In ethanol; water; for 3h;Reflux; | General procedure: Components 8-14 were prepared by condesation of <strong>[497-18-7]carbohydrazide</strong> (10 mmol) in ethanol(40 ml) and appropriate aldehydes or ketones (21 mmol) dissolved in ethanol (10 ml) underreflux for 3 h with addition of one drop of conc. hydrochloric acid. After completion ofreaction, the resulting precipitate was collected by filtration and washed successively withcold alcohol, ethyl ether, dried and recrystallized from a suitable solvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium acetate In ethanol for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol; at 20℃; for 72h;Heating; | General procedure: Compound 1 or 2, 3 mmol, was slowlyadded dropwise to a solution of 3 mmol of carbonic hydrazide 3 in a minimum volume of anhydrousethanol (compound 3 was dissolved on heating). Themixture was kept for 3 days at room temperature. Inthe synthesis of 4, the solvent was removed at roomtemperature, and the residue was recrystallized fromhexane. Compound 5 separated from the reaction mixtureand was filtered off and washed with anhydrous ethanol. 5-Hydroxy-3-methyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-1-<strong>[497-18-7]carbohydrazide</strong> (4). Yield60%, mp 165C; published data: mp 161-162C [3],158-159C [8]. 1H NMR spectrum, delta, ppm: 1.96 s(3H, Me), 2.99 d and 3.35 d (1H each, 4-H, 2J =19.0 Hz), 4.07 br.s (2H, NH2), 7.38 br.s (1H, NH),7.87 br.s (1H, OH). 13C NMR spectrum, deltaC, ppm:15.98 (Me), 48.56 (C4), 91.36 q (C5, 2JCF = 33.1 Hz),124.27 q (CF3, 1JCF = 285.1 Hz), 152.60 (C3), 156.02(C=O). Found, %: C 31.97; H 3.89; N 24.29.C6H9F3N4O2. Calculated, %: C 31.86; H 4.01; N 24.77. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; water; at 20℃; for 8h; | Three pyridine-urea isomer 2L, 3L and 4L was synthesized ingood yield following the reported literature procedure [57]. Whitecrystalline <strong>[497-18-7]carbohydrazide</strong> (0.180 g, 2 mmol) was taken in roundbottom flask containing 2 mL of water and heated to dissolve thesolid powder. Then 40 mL methanolic solution of pyridine-2-aldehyde(0.380 mL, 4 mmol) was added to the clear solution andfinally stirred the whole reaction mixture for 8 h. After completionof reaction solvent was evaporated under vacuum that left slightyellow semi-solid mass. After drying in desiccator it gave yellowishsolid product of 2L [33]. Preparation of other isomers (3L and 4L) issimilar to that of 2L (Scheme S1). |
With hydrogenchloride; In ethanol; water; for 3h;Reflux; | General procedure: Components 8-14 were prepared by condesation of <strong>[497-18-7]carbohydrazide</strong> (10 mmol) in ethanol(40 ml) and appropriate aldehydes or ketones (21 mmol) dissolved in ethanol (10 ml) underreflux for 3 h with addition of one drop of conc. hydrochloric acid. After completion ofreaction, the resulting precipitate was collected by filtration and washed successively withcold alcohol, ethyl ether, dried and recrystallized from a suitable solvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.6% | With acetic acid; In ethanol; for 4h;Reflux; | 1.0 mmol carbazide, 2.1 mmol 4-hydroxybenzaldehyde, 2 drops of acetic acid and 16 mL of ethanol were refluxed for 4 h, and the reaction was monitored by TLC. The reaction solution was cooled to room temperature, filtered with suction, and the filter cake was washed with petroleum ether and ethanol, and dried to obtain bis(4-hydroxybenzaldehyde)carbonyldihydrazone (Ia), white solid, mp198-199 C, yield 89.6%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrazine hydrate; In methanol; water; at 75℃; for 0.000833333h; | Dissolving dimethyl carbonate in methanol, Made into a 3mol/L solution, It was injected into the microchannel reactor or the pipeline reactor through a metering pump at a flow rate of 30 ml/min. 80% by mass of aqueous hydrazine hydrate solution was passed through another metering pump at 11.26 ml/ The flow rate of min is injected into the microchannel reactor or the pipeline reactor, React at 75 C for 3 seconds, Flow out of the microchannel reactor or pipeline reactor, Collecting reaction materials, Obtaining a white crystalline product, Yield 99%, 99.9%, The monoterpene content is 0.01%. |
89.1% | With hydrazine hydrate; acetic acid; In ethanol; for 3h;Reflux; | 6.0mmol of dimethylcarbonate and 24.0mmol of 80% hydrazinehydrate were placed in 16mL of ethanol and reacted for 3h; the reaction mixture was cooled to room temperature, and then filtered with suction. The filter cake was washed with petroleum ether and ethanol and dried to obtain carbazide89.1% yield. |
85% | With hydrazine; In methanol; at 70 - 80℃; for 8h; | 1) In a 2000 mL reaction flask, a stirrer, a thermometer, a constant pressure dropping funnel, and a condenser were installed. 540 mL of dimethyl carbonate was added at room temperature, stirring was started, and a methanol solution containing hydrazine was added (the volume fraction of hydrazine accounted for 60%)1000 mL, the reaction was stopped after refluxing at 70 C for 4 h,The unreacted dimethyl carbonate and methanol were recovered by distillation under reduced pressure, and 650 mL of a methanol solution containing hydrazine was added to the residue, and the reaction was vigorously refluxed at 80 C for 4 hours, cooled to room temperature, stirred, and precipitated.White solid, suction-filtered to give a white solid eluting with a small methanol (100 mL×3).Dry to give 460 g of a white solid.Yield85%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.5% | With sodium sulfate; In ethanol; for 4h;Heating / reflux; | [0407] The ligand was prepared using the method described by Exner O; Kliegman, J M; J. Org. Chem. 1971, 36, 2014-2015. [0408] 8.96 g of anhydrous sodium sulphate (63.1 mmoles) and 4.0 ml of 2-pyridylaldehyde (42.05 mmoles) were added in succession to a suspension of 1.89 g of <strong>[497-18-7]carbohydrazide</strong> (21.0 mmoles) in 150 ml of absolute ethanol. [0409] The reaction mixture was heated for 4 hours under reflux then filtered through a frit (the disappearance of the 2-pyridylaldehyde was monitored by gas chromatography). [0410] The retained solid was washed with copious amounts of absolute ethanol to dissolve the product obtained. [0411] The filtrate was concentrated to isolate a colourless solid, which was oven dried at 100 C. then re-crystallised from methanol. [0412] 4.53 g of colourless crystals were obtained, corresponding to a yield of 80.5%. [0413] The characteristics were as follows: [0414] M.Pt: 219-220 C.; [0415] 1H NMR/DMSO-d6: delta 11.08 (wide s, 2H, NH), 8.58 (m, 2H, H2,13), 8.25 (wide s, 2H, H6,), 8.12 (m, 2H, H5,10), 7.87 (m, 2H, H4,11), 7.38 (m, 2H, H3,12); [0416] 13C NMR/DMSO-d6: delta 153.46 (C7), 151.64 (C1 and C19), 149.26 (C2 and C13), 143.69 (C6 and C8), 136.52 (C4 and C11), 123.83 (C3 and C12), 119.75 (C5 and C10); [0417] FAB+ (NBA matrix): 269 (60%, M+1), 148 (51%, [C5H4NCHN-NHCO]+), 122 (44%, C5H4N-CHN-NH3+), 107 (41%, 2-pyridylaldimine+H+), 537 (4%, 2M+1), 559 (1%, 2M+Na+). |
80.5% | With sodium sulfate; In ethanol; for 4h;Heating / reflux; | 8.96 g of anhydrous sodium sulphate (63.1 mmoles) and 4.0 ml of 2-pyridylaldehyde (42.05 mmoles) were added in succession to a suspension of 1.89 g of <strong>[497-18-7]carbohydrazide</strong> (21.0 mmoles) in 150 ml of absolute ethanol. The reaction mixture was heated for 4 hours under reflux then filtered through a frit (the disappearance of the 2-pyridylaldehyde was monitored by gas chromatography). The retained solid was washed with copious amounts of absolute ethanol to dissolve the product obtained. The filtrate was concentrated to isolate a colourless solid, which was oven dried at 100 C. then re-crystallised from methanol. 4.53 g of colourless crystals were obtained, corresponding to a yield of 80.5%. The characteristics were as follows: M.Pt: 219-220 C.; 1H NMR/DMSO-d6: delta 11.08 (wide s, 2H, NH), 8.58 (m, 2H, H2,13), 8.25 (wide s, 2H, H6,8), 8.12 (m, 2H, H5,10), 7.87 (m, 2H, H4,11), 7.38 (m, 2H, H3,12); 13C NMR/DMSO-d6: delta 153.46 (C7), 151.64 (C1 and C19), 149.26 (C2 and C13), 143.69 (C6 and C8), 136.52 (C4 and C11), 123.83 (C3 and C12), 119.75 (C5 and C10); FAB+ (NBA matrix): 269 (60%, M+1), 148 (51%, [C5H4NCHN-NHCO]+), 122 (44%, C5H4N-CHN-NH3+), 107 (41%, 2-pyridylaldimine+H+), 537 (4%, 2M+1), 559 (1%, 2M+Na+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate In water; phenol | 7 Compound No. I-2 STR13 Analogously to Example 3, a solution of carbodihydrazide in phenol is prepared from 2,264 g (10.6 mol) of diphenyl carbonate and 1,058 g (21.2 mol) of hydrazine hydrate and is substantially dehydrated under reduced pressure. After addition of 1 g of dimethyltin oxide and 803 g (11.6 mol) of isobutyronitrile, the mixture is heated under reflux for 10 hours (initial temperature 138° C., final temperature 185° C.). The volatile components are then distilled off under reduced pressure and the residue is dissolved in 1.5 L of hot water. 116 g (1.6 mol) of diethylamine are added at 80° C. and the amine which has not been consumed and residual phenol are then distilled off. After cooling to 10° C., the product is filtered off with suction, washed with cold water and dried. 1,129 g (75% of theory) of 3-isopropyl-4-amino-1,2,4-triazol-5-one of melting point 172° C. are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | EXAMPLE 14 N-(1-Carboxy-3-phenylpropyl)-alpha-azaalanyl-(L)-proline t-butyl ester (18) A solution of carbazide 2 (0.243 g; 1.00 mmol) and 4-phenyl-2-oxobutanoic acid (0.534 g; 3.00 mmol) in water (1 ml) was adjusted to pH=7 by addition of aqueous sodium hydroxide (2N). Then a solution of sodiumcyanoborohydride (0.0628 g; 1.00 mol) in water (1 ml) was added over a period of 4 hours. Stirring was continued for 48 hours. Water-washed DOWEX 50W-X4 resin (3 g) was added and stirring was continued for 90 minutes. The mixture was then diluted with water-CH3 OH(1:1; 5 ml) and transferred to a column of the same resin (5 g). Elution was carried out with H2 O--CH3 OH (10:1) and then H2 O-pyridine (50:1). The latter solvent mixture brought about elution of pure azapeptide ester 18 (0.300 g; 0.742 mmol; 74%) as a white foam after freeze-drying. TLC (silica gel; EPAW, 20:5:1:1), RF=0.6. MS m/e 477 (M+, monotrimethylsilyl). NMR (CDCl3); delta1.43 (9H,S); 1.7-2.3 (6H,m); 2.6-3.0 (2H,m); 3.00 (3H,s); 3.4-3.7 (2H,m); 4.3-4.6 (1H,m); 7.20 (5H,s); 7.25 (2H,bs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | A solution of <strong>[497-18-7]carbohydrazide</strong> (82 mg, 0.92 mmol) in DMF (1 mL) was added dropwise to a solution of Boc-DLeu-OH (57 mg, 0.23 mmol) and PyBOP (143 mg, 0.275 mmol) and DIEA (80 muL, 0.46 mmol) in DMF (1 mL). The reaction.was stirred at room temperature under nitrogen for 3 hours and the solvents were removed under reduced pressure. The resulting residue was purified by HPLC on a Phenomenex Luna Cl 8 column (21.2 x 250 mm) using a 0.9%/min gradient of 9 to 36% acetonitrile containing 0.1% TFA at a flow rate of 20 mL/min. The main product peak eluting at 19.5 minutes was lyophilized to give the title compound as a colorless solid (61 mg, 87%, HPLC purity 100%). 1H NMR (1:1 CD3CN:D2O): delta 8.60 (bs, IH), 7.62 (bs, IH), 5.62 (s, IH)5 4.10 (s, IH), 1.73-1.62 (m, IH), 1.61-1.48 (m, 2H), 1.42 (s, 9H), 0.96-0.88 (m, 6H); 13C NMR (CDCl3): delta 174, 160, 157, 52.9, 41.6, 28.8, 25.4, 23.6, 22.1. MS (ESI): 607.4 (10, 2M+H), 248.4 (100, M-tBu+H), 204.4 (60, M-Boc+H); HRMS: Calcd for C12H26N5O4 (M+H): 304.1979; Found: 304.1975. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In deuteromethanol; water; for 0.5h;Heating; | General procedure: 3,5,12,14-dipyridyl 8,9,17,18-dibenzo[2,4,6,11,13,14 hexacyclo octadecane 1,6,10,15 tetraene[PBCODT][L1]. o-phthalaldehyde (5.36 g, 0.04 mol.) dissolved in 25 ml aqueous methanol solution (1:1) was added to a 25 ml aqueous methanol solution (1:1) of 2,6-diaminopyridine (4.4 g, 0.04 mol.) with constant stirring on a hot plate stirrer for 30 min. The light brown colored precipitate formed was filtered, washed with cold methanol, diethyl ether, recrystalized from ethanol and dried in vacuum. The product was found to be TLC pure in 8:2 chloroform and methanol mixture. Our synthetic route of Schiff base ligands is shown in Scheme 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In water; acetonitrile; at 20℃; for 1h; | Gold cyanide (AuCN, 2.23 g, 10 mmol) is dissolved in 10 mL of acetonitrile in a 50 mL round Schlenk flask to form a gold cyanide solution, and a solution of carboxyhydrazide (H2NHNCONHNH2, 0.90 9, 10 mmol) in 5 mL of water is added dropwise to the gold cyanide solution. Subsequently, propyl amine (1.20 g, 20 mmol) is slowly added dropwise to the mixture, stirred at room temperature for about one hour and the contents of the Schlenk flask are filtered to remove a small amount of impurities. Hexane is added to the solution retained in the Schlenk flask and the solution is precipitated to obtain the target compound, Au(CN) (n-PrNH2) [H2NHNCONHNH2] The reaction yield for the target compound is 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In water; acetonitrile; for 1h; | Copper nitrate (Cu(NO3)2, 1.87 grams (g), 10 millimoles ("mmol") is dissolved in 5 milliliters ("mL") of acetonitrile in a 50 mL round Schlenk flask, and a solution of carboxyhydrazide (H2NHNCONHNH2, 0.90 g, 10 mmol) in 5 mL of water is added dropwise to the copper nitrate solution. The reaction is allowed to proceed for one hour with stirring. Then, the reaction mixture in the Schlenk flask is filtered to remove a small amount of impurities. Subsequently, hexane is added to the remaining solution in the Schlenk flask and the solution is precipitated to obtain the target compound, Cu(NO3)2[H2NHNCONHNH2]. The reaction yield for the target compound is 93%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | A solution of <strong>[497-18-7]carbohydrazide</strong> (1.8018 g, 0.02 mol) in water (15 mL) was heated for 15 min in presence of few drops of acetic acid and then was added to a hot solution of benzil (2.1023 g, 0.01 mol) in ethanol (15 mL). The reaction mixture was refluxed for 2 h at 65 C, allowed to stay at room temperature and then kept in refrigerator overnight. The white product was precipitated out, which was filtered off, washed several times with ethanol and dried under vacuum over P4O10. Yield 80%, m.p. 206 C. Elemental analyses, Found (Calcd.) For C16H18N8O2: C, 54.29 (54.24); H, 5.12 (5.08); N, 31.70 (31.64)%. 1H NMR (300 MHz, DMSO-d6): d (ppm): 4.29 (S, 4H, 2 NH2), 9.68 (S, 4H, 4NH), 7.15-7.95 (m, 10H, 2Ph); 13C NMR (300 MHz, DMSO-d6): d (ppm): 125.98-135.54 (m, 12C, 2 Ph), 151.09 and 151.27 (2C, AC(at)NA), 160.22 and 161.20 (2C, AC(at)ONHA). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; In ethanol; water; for 6h;Reflux; | Synthesis of ionophore dibenzoylmethane bis(carbohydrazone) (BMBC) An aqueous ethanolic solution of <strong>[497-18-7]carbohydrazide</strong> (0.02 mol, 1.80 g) was treated with 1 ml glacial acetic acid followed by slow addition of a solution of dibenzoylmethane (0.01 mol, 2.24 g) in 20 ml ethanol. The resulting mixture was heated under reflux for about 6 h. On cooling overnight at 0 C, white crystalline precipitate of BMBC was separated out, which was filtered, washed with cold ethanol and dried under vacuum. Yield 81%, m.p. 182-185 C. Elemental analysis: C17H20N8O2, Found (Calc.) C: 55.44 (55.13), H: 5.43 (5.08), N: 30.43 (30.17). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In methanol; for 6h;Reflux; | A methanol (10 mL) solution of <strong>[497-18-7]carbohydrazide</strong> (0.50 g, 5.55 mmol) was drop-wise added to a methanol solution (10 ml) of 2-acethylpyridine (1.34 g, 11.10 mmol) and the mixture was refluxed for 6 h. Then the solution was evaporated on a steam bath to 5 cm3 and cooled to room temperature. Resulting white precipitate was separated and filtered off, washed with 5 mL of cooled methanol and re-crystallized. Yield: 95% (1.56 g). |
95% | In methanol; for 6h;Reflux; | A methanol (10 mL) solution of <strong>[497-18-7]carbohydrazide</strong> (0.50 g, 5.55 mmol) was added dropwise to a methanol solution (10 mL) of 2-acetylpyridine (1.34 g, 11.10 mmol) and the mixture was refluxed for 6 h. The solution was evaporated on a steam bath to 5 mL and cooled to room temperature. The resulting white precipitate was separated and filtered off, washed with 5 mL of cooled methanol and recrystallized. Yield: 95% (1.56 g). Anal. Calc. for C15H16N6O (MW = 296.33): C, 60.80; H, 5.44; N, 28.36. Found: C, 60.73; H, 5.46; N, 28.42%. FT-IR (KBr, cm-1): 3445 (m, br), 3355 (m), 3206 (m, N-H), 3061 (m), 2923 (m), 1700 (vs C=O), 1680 (vs), 1578 (m), 1518 (s), 1462 (s), 1433 (s), 1310 (w), 1261 (s), 1132 (s), 991 (w), 808 (m), 788 (s), 739 (m), 598 (w), 528 (w), 441 (w), 404 (w). 1H NMR (250.13 MHz, DMSO-d6, TMS) delta (ppm): 10.87 (s, 2H, N-H), 8.61 (d, 2H, J = 7.25 Hz), 8.12 (d, 2H, J = 7.5 Hz), 7.91 (m, 2H), 7.43 (t, 2H, J = 7.5 Hz), 2.45 (s, 6H). 1H NMR (250.13 MHz, DMSO-d6 + D2O) delta (ppm): 7.39-8.70 (10 H, aromatic), 2.59 (s, 6H). 13C NMR (62.90 MHz, DMSO-d6) delta (ppm): 12.4, 120.8, 124.7, 136.4, 144.9, 149.1, 152.1, 157.3. UV-Vis (in CH3OH, c = 5 * 10-5 mol dm-3, lambdamax [nm] with epsilon [M-1 cm-1]): 214 (33 000), 298 (36 000), 380sh (5600). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol; at 70℃; for 6h; | General procedure: Carbohydrazide1.0 mmol (0.090 g) in 20 mL of ethanol was added to a solution of pentaflurobenzaldehyde(2.0 mmol, 0.392g) in 10 mL of ethanol and the mixture was slowly refluxed for 6 h at 70 C. After cooling to room temperature, white solid thus obtained was filtered and washed with ethanol followed by diethyl ether and then dried in vacuo. Yield: 0.379 g (85%). m.p.: 226-227 C. Anal. Calc. for C16H8N4O2F10: C,38.25; H, 6.42; N, 11.15; Found: C, 38.56; H, 6.12; N, 10.97. IR (KBr pellet, cm-1): 3242(m)upsilon(N-H), 1651(s) upsilon(C=O), 1595(s) upsilon(CH=N). 1H NMR (DMSO-d6, delta ppm): 11.09 (s, 2H; NH), 8.22 (s, 2H; CH=N). UV-vis(DMSO, 10-5 M): lambdamax (nm) (epsilonmax M-1 cm-1) 301 (36200) ( n-pi*). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: All the complexes were synthesized by template method since any attempt to isolate the free macrocyclic ligand was unsuccessful. To a hot, well-stirred methanolic solution (?50cm3) of <strong>[497-18-7]carbohydrazide</strong> (10mmol), divalent cobalt, nickel, copper and zinc salts (hydrated) (Cl-, NO3-, CH3COO-) (5mmol) dissolved in minimum quantity of methanol were added. The resulting solution was refluxed for 0.5h. Subsequently, isatin (10mmol) dissolved in ?20cm3 methanol was added in the refluxing mixture and refluxing was continued for 8-10h. The mixture was concentrated to half its volume, cooled to room temperature and kept in desiccator overnight. After overnight standing, dark coloured precipitates separate out, which were filtered, then washed with methanol, acetone, and ether and dried in vacuo. The obtained yields were ?60-75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 20℃; for 2h; | General procedure: Carbohydrazones 1-7 were prepared by reactions of <strong>[497-18-7]carbohydrazide</strong> (1,3-diaminourea,10 mmol) and appropriate aldehydes and ketones (5 mmol) in water (10 ml) at room temperaturewith addition one drop of conc. hydrochloric acid. Reaction mixture was stirred for 2h and the resulting precipitate was collected by filtration, and recrystallized from a suitablesolvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.3% | With trilithium citrate; In tetrahydrofuran; diethyl ether; hexane; ethyl acetate; | Example 9 Preparation of 3-(4-chlorophenyl)-5-(furan-2-yl)-1,3,4-oxadiazol-2(3H)-one (Formula Ia-v) To a suspension of 1-(4-chlorophenyl)hydrazine as the hydrochloride salt (89.5 mg, 0.5 mmol) in Et2O (4 mL) was added a 2 N solution of LiOH (1 mL), and the resulting mixture was stirred for 15 minutes. After the system became homogeneous, the organic layer was separated and dried over Na2SO4. The resulting ethereal solution of <strong>[497-18-7]carbohydrazide</strong> as a free base was cooled to -5 C., and then a solution of furan-2-carbonyl chloride (65 mg, 0.5 mmol) in 5 mL of THF was added dropwise to the resulting mixture. After stirring at 0 C. for 30 minutes, the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL). The organic layer was then separated, washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (5-50% EtOAc in hexane) to provide 100 mg (0.382 mmol, yield 76.3%) of 3-(4-chloro-phenyl)-5-furan-2-yl-3H-[1,3,4]oxadiazol-2-one with an HPLC purity of 99.9%. LC-MS [M+H] 263.7 C12H7ClN2O3+H, expected 263.01). The 1H-NMR spectrum was in accordance with the chemical structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In methanol; for 6h;Reflux; | A methanol (10 mL) solution of salicylaldehyde (0.73 g, 6.00 mmol) was drop-wise added to a methanol solution (10 mL) of <strong>[497-18-7]carbohydrazide</strong> (0.27 g, 3.00 mmol) and the mixture was refluxed for 6 h. The solution was then evaporated on a steam bath to 5 mL and cooled to room temperature. The resulting white precipitate was separated and filtered off, washed with 5 mL of cooled methanol and recrystallized from ethanol. Yield: 94% (0.84 g). M.p. 223-224.2 C. Anal. Calc. for C15H14N4O3 (MW = 298.30): C, 60.40; H, 4.73; N, 18.78. Found: C, 60.37; H, 4.70; N, 18.81%. IR (KBr, cm-1): 3417 (m, br), 3265 (vs br), 3159 (s), 1717 (vs), 1686 (s), 1624 (m), 1550 (m), 1490 (s), 1405 (s), 1352 (vs), 1271 (vs), 1217 (s), 1189 (m), 1157 (m), 1114 (m), 1034 (m), 958 (vs), 911 (m), 821 (s), 761 (s), 732 (m), 644 (m), 576 (m), 530 (m), 479 (m), 442 (w). 1H NMR (250 MHz, DMSO-d6, TMS) delta: 10.88 (s, 2H, O-H, N-H), 8.43 (s, 1H, CH=N), 7.68 (s, 1H), 7.19 (t, 1H, J = 7.25 Hz), 6.85 (m, 2H). 13C{1H} NMR (62.9 MHz, DMSO-d6) delta: 157.01 (C=O), 152.4 (CH=N), 143.27 (C-OH), 131.1, 128.6, 120.1, 119.6, 116.6. UV-Vis (in CH3OH, c = 5 * 10-5 M, lambdamax [nm] with epsilon [M-1 cm-1]): 219 (29.1 * 103), 292 (26 * 103), 330 (33 * 103). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In water; acetonitrile; at 40℃; for 18h; | ReferenceExample 2 - Synthesis of Mercaptobutyric Acid Carbohydrazide (MBCH) (0039) In another particular example, not forming part a of the invention, a <strong>[497-18-7]carbohydrazide</strong> thiol linker was prepared from gamma-butyrothiolactone according to Scheme 7. (0040) In particular, gamma-butyrothiolactone (0.43 ml, 5 mmol) was diluted in acetonitrile (5 ml) and then slowly added to a solution of <strong>[497-18-7]carbohydrazide</strong> (2.25 g, 25 mmol) in deionized water (5 ml). The reaction was stirred at 40C for 18 h, and then concentrated in vacuo. The crude product was removed by filtration with acetonitrile and flash chromatography (SiO2, 1:19 MeCN / MeOH) to give the product as a white solid. Yield: 672 mg (70%): 1H NMR (250 MHz, D2O) delta 2.62-2.56 (t, J= 7.1 Hz, 2 H), 2.47-2.41 (t, J= 7.4 Hz, 2 H), 1.98-1.87 (m, 2 H); 13C NMR (62.9 MHz, D2O) delta 179.14, 163.94, 34.86, 31.74, 25.91; ESI-HRMS m/z 215.05818 (M + Na+, C5H12N4NaO2S calc'd 215.25787). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; N,N-dimethyl-formamide; at 225℃; for 9h; | The ligand N-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-N'-[1-(2-hydroxy-5-methyl-3-nitrophenyl)ethylidene] carbonohydrazide was prepared by dropwise addition of equimolar amountsof 5-chloro-2-hydroxy acetophenone (2.4 g, 0.016 mol) to 2-hydroxy-5-methyl-3-nitroacetophenone (3.12 g, 0.016 mol) with stirring at room temperature. This resulting reactionmixture was reacted with a hot ethanol-DMF solution (60:40 v/v; 25 mL) of <strong>[497-18-7]carbohydrazide</strong>(1.44 g., 0.016 mol) and mixture was refluxed on sand bath for about 9 h at 225 oC. The solventwas then partially evaporated in air and faint yellow coloured compound obtained was filteredand washed it with ethanol, petroleum ether and dried in vacuum over anhydrous CaCl2. Thesynthesized ligand was crystallized and conformed though its melting point 313 oC (yield: 72%)and its NMR analysis as follows: 12.68 (S, 1H, OH, phenolic), 14.30 (S, 1H, OH, phenolic),10.19 (S, 1H, imino, NH), 10.23 (S, 1H, imino, NH), 2.12 (S, 3H, Ar-CH3), 2.31 (S, 3H, CH3),2.36 (S, 3H, CH3), 6.91-7.95 (m, 5H, aryl-H). The schematic representation of the synthesis ofligand H2L is shown in Figure 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With acetic acid; In ethanol; for 3h;Reflux; | A hot solution of o-tosylaminobenzaldehyde (0.006 mol) in 5 mL of ethanol was added to a hot solution of <strong>[497-18-7]carbohydrazide</strong> (0.003 mol) in 15 mL of ethanol. Four drops of glacial acetic acid were added to the obtained mixture, and it was refluxed during 3 h. The formed precipitate was filtered off, washed with ethanol, and recrystallized from a DMF-isopropanol mixture. Yield 65%, mp>250. IR spectrum, nu, cm-1: 3083 (N-H), 3210 (N-H),3363 (N-H), 1688 (C=O), 1615 (C=N), 1160 (SO2),1276 (SO2). 1NMR spectrum (DMSO-d6), delta, ppm:2.2 s (6, 23), 6.8-7.1 m (8arom), 7.2 d (4arom, 3J8.0 Hz), 7.7 d (4arom, 3J 8.0 Hz), 8.23 s (2, 2CH=N),10.6 s (2H, NH), 10.8 s (2H, NH). Found, %: C 57.15;H 4.21; N 14.37. C29H28N6O5S2. Calculated, %: C57.6; H 4.67; N 13.90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Carbon disulphide (6.04 ml, 0.1 mol) was added dropwise to a 90% ethanolic solution of<strong>[497-18-7]carbohydrazide</strong> (9.01 g, 0.1 mol) and potassium hydroxide (5.61 g, 0.1 mol) at a temperature below 5 C. Upon completion ofthe addition of carbon disulphide, benzyl chloride (11.51 ml, 0.1 mol) was added to the solution with vigorous stirring to givea white precipitate. The precipitate formed was filtered, washed with cold ethanol and dried under silica gel and recrystallizedin ethanol. Crystals were obtained by slow evaporation from ethanol. Yield: 65%, m.p. 93.7-95.1 C. Anal. Calc. forC16H18N4OS2: C 55.5, H 5.2, N 16.2; found C 55.0, H 5.8, N 16.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In ethanol; at 20℃; for 72h;Heating; | General procedure: Compound 1 or 2, 3 mmol, was slowlyadded dropwise to a solution of 3 mmol of carbonic hydrazide 3 in a minimum volume of anhydrousethanol (compound 3 was dissolved on heating). Themixture was kept for 3 days at room temperature. Inthe synthesis of 4, the solvent was removed at roomtemperature, and the residue was recrystallized fromhexane. Compound 5 separated from the reaction mixtureand was filtered off and washed with anhydrous ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In a 50 ml egg plant type flask,After adding 547 mg (6.1 mmol) of <strong>[497-18-7]carbohydrazide</strong>, 6 ml of water and 0.05 ml of 12N hydrochloric acid and stirring using a magnetic stirrer for 10 minutes at room temperature, 900 mg (16.1 mmol) of acrolein was added and further stirring was continued at room temperature did. After the start of stirring, crystals precipitated immediately and after stirring for 2 hours, 20 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution. Precipitated crystals were collected by filtration, washed with water and then dried in vacuo at 50 C. for 20 hours to obtain 0.62 g (3.7 mmol) of a white solid. 5. The obtained solid was analyzed by 1 H-NMR and confirmed to be bis(allylideneamino)urea . The molar yield was 62% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In a 50ml eggplant type flask,1.07 g (11.9 mmol) of <strong>[497-18-7]carbohydrazide</strong>, 12 ml of water and 0.1 ml of 12N hydrochloric acid were added and stirred for 10 minutes at room temperature using a magnetic stirrer, and then 2.02 g (28.8 mmol) of methacrolein was added thereto. To the reaction mixture was added 20 ml of a saturated aqueous solution of sodium bicarbonate, and the precipitated crystals were collected by filtration, washed with water and dried at 50 C. for 20 minutes at 50 C. After stirring for 1 hour, crystals were precipitated and stirred for 1 hour, Dried to obtain 2.23 g (11.5 mmol) of a white solid, which was analyzed by 1 H-NMR to be bis(2-methylallylideneamino)urea |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | 1.07 g (11.9 mmol) of <strong>[497-18-7]carbohydrazide</strong> 12 ml of water and 0.1 ml of 12N hydrochloric acid were added to a 50 ml eggplant type flask and stirred using a magnetic stirrer for 10 minutes at room temperature. Then, 1.73 g of crotandaldehyde(24.5 mmol), and stirring was continued at room temperature.After the start of stirring, crystals precipitated immediately, and after stirring for 1 hour, 20 ml of water was added to the reaction solution.The precipitated crystals were collected by filtration, And dried under vacuum at 50 C. for 20 hours to obtain 2.22 g (11.4 mmol) of a white solid, which was analyzed by 1 H-NMR to confirm that it was bis(2-butenylideneamino)urea.the molar yield was 96%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 20℃; for 2h; | General procedure: Carbohydrazones 1-7 were prepared by reactions of <strong>[497-18-7]carbohydrazide</strong> (1,3-diaminourea,10 mmol) and appropriate aldehydes and ketones (5 mmol) in water (10 ml) at room temperaturewith addition one drop of conc. hydrochloric acid. Reaction mixture was stirred for 2h and the resulting precipitate was collected by filtration, and recrystallized from a suitablesolvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 20℃; for 2h; | General procedure: Carbohydrazones 1-7 were prepared by reactions of <strong>[497-18-7]carbohydrazide</strong> (1,3-diaminourea,10 mmol) and appropriate aldehydes and ketones (5 mmol) in water (10 ml) at room temperaturewith addition one drop of conc. hydrochloric acid. Reaction mixture was stirred for 2h and the resulting precipitate was collected by filtration, and recrystallized from a suitablesolvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 20℃; for 2h; | General procedure: Carbohydrazones 1-7 were prepared by reactions of <strong>[497-18-7]carbohydrazide</strong> (1,3-diaminourea,10 mmol) and appropriate aldehydes and ketones (5 mmol) in water (10 ml) at room temperaturewith addition one drop of conc. hydrochloric acid. Reaction mixture was stirred for 2h and the resulting precipitate was collected by filtration, and recrystallized from a suitablesolvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.26% | With triethylamine; In N,N-dimethyl-formamide; toluene; at 105.0℃; for 6.0h; | Reactor Was added 200mg (0.6mmol) in the reactor <strong>[87080-27-1]licochalcone A</strong> and 69.21mg (1.3mmol)carbohydrazide, 50ml of toluene as a reaction solvent and 5mLDMF, 0.5mL of triethylamine was added as the catalyst is heated, the heating units 105 , magnetically stirred and refluxed for 6 hours. The reaction was followed by thin layer chromatography. After completion of the reaction, concentrated under reduced pressure, column chromatography, stripped to dryness to give a brown powder (117.08mg), total yield of 48.26%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; at 20℃; for 2h; | This was prepared by modifying the reported method of Bustoset al. [29]. Salicylaldehyde (20 mmol) was added to a solution of<strong>[497-18-7]carbohydrazide</strong> (10 mmol) dissolved in 50 mL of methanol, andthe resulting reaction mixture was stirred at RT for 2 h, filteredthrough a G-3 crucible and the pale white solid was washed wellwith methanol and air dried. Yield 80%; mp 226 C. Anal. Calc. forC15H14N4O3: C, 60.40; H, 4.73; N, 18.78. Found: C, 61.01; H, 4.68;N, 18.51%. Recrystallization of this compound from methanol-ethanol(1:1) mixture led to formation of colorless single crystals suitablefor X-ray diffraction. We have characterized it by X-ray crystalstructure (vide infra). |
70% | In ethanol; at 20℃; for 2h; | This compound was prepared by the reported method ofKoley et al. [41]. To a stirring solution of <strong>[497-18-7]carbohydrazide</strong>(5 mmol) dissolved in 30 mL of absolute ethanol, salicylaldehyde(10 mmol) was added dropwise at RT and thereaction mixture was stirred at RT for 2 h while a white compoundseparated. This was filtered through a G-3 crucibleand the pale white solid was washed well with ethanol andair dried. This compound was recrystallized from methanol-ethanol (1:1). Yield 70%; mp 226 C. Anal. Calc. forC15H14N4O3:C, 60.40; H, 4.73; N, 18.78. Found: C, 60.57;H, 4.76; N, 18.81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The title compound of PREPARATION 51(100 mg, 0.39 mmol) was suspended in 3 ml dichloromethane. (Benzotriazol-1 -yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP, 180 mg, 0.41 mmol) was added and the mixture was stirred for 5 mi Triethylamine (0.14 ml, 1 mmol) was added, dissolving the suspension. Hydrazinecarboxamide (45 mg, 0.40 mmol) was added and the mixture was stirredovernight at room temperature forming a precipitate. The solid was collected by filtration to give 105mg of the crude title compound. Purity 81%.UPLC/MS (3 mm) retention time 0.99 mm.LRMS: mlz 280 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With acetic acid; In ethanol; at 80℃; under 760.051 Torr; for 3h; | S1. 1.0 mmol of 1-pyrene Formaldehyde is dissolved in 10 mL of absolute ethanol, 1.0 mmol of carbonic acid dihydrazide is added, and 0.5 mol% of glacial acetic acid is added to prepare a mixed solution.S2. The mixture was warmed to 80 C, under normal pressure and refluxed for 3h.S2. After cooling to room temperature, the solid precipitated and was filtered under reduced pressure. The residue was washed with absolute ethanol to give the desired acylhydrazone compound containing a pyrenyl group (a yellow solid in a yield of 79%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With acetic acid; In methanol; at 75℃; under 760.051 Torr; for 4h; | S1. 1.0 mmol of 6-isopropyl-1-pyrene Formaldehyde was dissolved in 10 mL of methanol,After adding 1.0 mmol of carbonic acid dihydrazide,And add 0.5mol% of glacial acetic acid,Made of mixed solution.S2. The mixed solution was warmed to 75 ,Under normal pressure, reflux for 4h.S2. After cooling to room temperature,Vacuum filtration,The residue is washed with anhydrous ethanol to give the desired acylhydrazone compound containing a pyrenyl group(Yellow solid, 71% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With acetic acid; In isopropyl alcohol; at 100℃; under 760.051 Torr; for 5h; | S1. 1.0 mmol of 1-pyrenylethyl ketone was dissolved in 10 mL of isopropanol,After adding 1.0 mmol of carbonic acid dihydrazide,And add 2mol% of glacial acetic acid, made of mixed solution.S2. The mixed solution was warmed to 100 C, stirred under reflux for 5h.S2. After cooling to room temperature, precipitated solid, filtered under reduced pressure,The residue is washed with anhydrous ethanol to give the desired acylhydrazone compound containing a pyrenyl group(Yellow solid, 46% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With acetic acid; In isopropyl alcohol; at 110℃; under 760.051 Torr; for 5h; | S1.1.0 mmol of 1-pyrenyl phenyl ketone was dissolved in 10 mL of isopropanol,Then add 1.2mmol of carbonic acid dihydrazide,And add 2mol% of glacial acetic acid,Made of mixed solution.S2. The mixed solution was warmed to 110 C.,The mixture was refluxed under atmospheric pressure for 5h.S2. After cooling to room temperature,Vacuum filtration,The residue is washed with anhydrous ethanol to give the desired acylhydrazone compound containing a pyrenyl group(Yellow solid, 49% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With acetic acid; In ethanol; at 85℃; under 760.051 Torr; for 4h; | S1. 1.0 mmol of 6-bromo-pyrene formaldehyde was dissolved in 10 mL of absolute ethanol,Then add 1.2mmol of carbonic acid dihydrazide,And add 1mol% of glacial acetic acid,Made of mixed solution.S2. The mixed solution was warmed to 85 C,Under normal pressure, reflux for 4h.S2. After cooling to room temperature,Vacuum filtration,The residue is washed with anhydrous ethanol to give the desired acylhydrazone compound containing a pyrenyl group(Yellow solid, yield 64%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With acetic acid; In methanol; at 70℃; under 760.051 Torr; for 3h; | S1. 1.0 mmol of 8-methoxy-1-pyrene formaldehyde was dissolved in 10 mL of methanol,After adding 0.8 mmol of carbonic acid dihydrazide,And add 1mol% of glacial acetic acid,Made of mixed solution.S2. The mixed solution was warmed to 70 C,Under normal pressure, reflux for 3h.S2. After cooling to room temperature,Vacuum filtration,The residue is washed with anhydrous ethanol to give the desired acylhydrazone compound containing a pyrenyl group(Yellow solid, 66% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.3% | In methanol; water; for 3h;Reflux; | A 200 mL (1.08 mmol) 6-methoxy-2-naphthaldehyde was placed in a 50 mL round bottom flask and dissolved with 10 mL of methanol.486mg (5.40mmol) of carbohydrazide dissolved in 10mL of water was added to the above solution, heated to reflux for 3 hours,The reaction product was cooled to room temperature to give a white precipitate which was filtered with suction and the precipitate was washed 3-4 times with water and then crystallized with methanol to give yellow needle crystals in a yield of 90.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol; under 760.051 Torr; for 4h;Reflux; | 8.82 g of <strong>[38707-70-9]quinoline-8-carbaldehyde</strong> was dissolved in 160 mL of 75% ethanol.Then add 2.75g of carbon dihydrazide,Under normal pressure, reflux and stir for 4h. After cooling to room temperature, a large amount of solids precipitated and was filtered under reduced pressure.The filter residue was washed with 75% ethanol to give a pale green solid, which was the target product.The yield of the target product is 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol; under 760.051 Torr; for 2h;Reflux; | 4.20 g of 3H-naphtho[2,1-b]pyran-2-carbaldehyde was dissolved in 200 mL of ethanol solution,Add 1.80g of <strong>[497-18-7]carbohydrazide</strong>,Stirring under reflux at normal pressure for 2 h,After cooling to room temperature, a large amount of solid was precipitated, and the mixture was filtered under reduced pressure, and the residue was washed with ethanol to obtain a yellow solid, which was the target product.The yield of the target product was 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; at 20℃; for 4h; | A solution of 5-chlorosalicylaldehyde (0.7829 g, 5.0 mmol) in absolute ethanol (10 mL) was added dropwise to a vigorous stirring solution of <strong>[497-18-7]carbohydrazide</strong> (0.9008 g, 10.0 mmol, 97%) in the same solvent(30 mL) at room temperature for 4 h (see Scheme 2). After that time,white precipitate was formed. The precipitate is collected and washed with distilled water to remove excess <strong>[497-18-7]carbohydrazide</strong> and dried to give 2 (yield: 82%). 1H NMR (DMSO, Fig. S1), delta (ppm, 600 MHz, TMS):10.445 (s, 2H), 8.209 (s, 1H), 8.110 (s, 1H), 7.970 (s, 1H), 7.184-7.170(d, 1H), 6.864-6.850 (d, 1H), 4.081 (s, 2H). 2 (0.93 g, 4.0 mmol) and 1-pyrenecarboxaldehyde (0.9211 g, 4.0 mmol) was dissolved in 30 mL absolute ethanol and the mixture was refluxed for 3 h. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was allowed to stand for several days to remove the filtrate by filtration and the pure product was obtained as a yellow solid 1 (yield: 32%) (Scheme 2). ESI mass spectrometry: m/z = 441.1112 [M + H]+,[M + H]+ calculated 441.11 (Fig. S2). 1H NMR (DMSO, Fig. S3), delta(ppm, 600 MHz, TMS): 11.112-11.055 (d, 2H), 9.312 (s, 1H), 8.793 (s,1H), 8.638 (s, 1H), 8.507 (s, 1H), 8.410-8.341 (m, 4H), 8.258-8.219(m, 2H), 8.126-8.101 (t, 2H), 7.842 (s, H), 7.289-7.275 (d, 1H),6.958-6.944 (d, 1H). Anal. Calcd for 1: C25H17ClN4O2 (%), C, 68.11; H,3.89; N, 12.71. Found (%): C, 68.04; H, 4.06; N, 12.74. The scanning electronic microscopy (SEM) measurement for power of 1 was shown in Fig. S4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | With sodium hydroxide; In water; at 60℃; for 0.333333h; | (2)At a temperature of 60 C,1.61g of 5,5'-dinitroamino-3,3'-linked-1,2,4-triazole,20 ml of a 1 mmol·ml-1 aqueous sodium hydroxide solution and 1.1 g of <strong>[497-18-7]carbohydrazide</strong> were added to the reaction flask, 5,5'-dinitroamino-3,3'-linked-1,2,4-triazole ,The molar ratio of sodium hydroxide to <strong>[497-18-7]carbohydrazide</strong> is 1:3:2.05, and the mixture is stirred for 20 minutes.Add 35% hydrochloric acid to a pH of 6,Reduce the temperature to 25 C,The white product 5,5'-dinitroamino-3,3'-linked-1,2,4-triazole carboxamide was precipitated in the system.1.82g,The calculated yield was 5,5'-diamino-3,3'-linked-1,2,4-triazole.87.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In neat (no solvent); at 20 - 90℃; for 0.5h; | The synthesis of compound (3) was performed in a facile way as per the literature-reported method. For this purpose, equimolar ratio (5 mmol) of both reactants (palmitic acid and <strong>[497-18-7]carbohydrazide</strong>) was thoroughly mixed by continuous stirring in a 100-ml round-bottom flask at room temperature. The reaction mixture was continuously stirred, and the temperature was gradually raised to 90 C for 30 min. Thin-layer chromatography was constantly used to monitor the progress of the reaction. Upon successful completion of the reaction, ice-cold water was added to the reaction mixture, and the mixture was placed in the freezer overnight. After 24 h, white-colored solid precipitates appeared slowly in the flask. The resulting solid precipitates were dried and filteredusing Buchner filter paper. The filtered solid precipitates were then further purified by recrystallization from chloroform and ethanol at room temperature [16]. 4-amino-5-pentadecyl-2H-1,2,4-triazol-3(4H)-one (3) (90-93%): m.p 135 C; Rf;0.54 (chloroform: methanol, 7:3); White powder; Mol. wt: 310.48; IR (Pure) nu: 3361.86, 3260.80 (NH2), 3330.39 (NH), 2954.04, 2872.10 (C=C-H), 2913.07, 2847.46 (-CH3), 1714 (CO), 1650 (NH Bending), 1538 (C=N), 1470 (-C-H Bending), 1427 (C-N), 1365 (-C-H Bending), 1078 (N-N), 718.02 (Long chain band), cm-1; 1H NMR (DMSO-d6, 400.13 MHz) delta: 7.12 (b, s, 1H, NH), 5.48 (b, s, 2H, NH2), 2.32 (t, 2H, J = 6.92 Hz, C-H), 2.19 (t, 2H, J = 6.92 Hz, C-H), 1.49 (m, 2H, C-H), 1.25 (m, 24 H), 0.868 (t, 3H, J = 6.96 Hz, C-H); 13C NMR (DMSO-d6, 100.55 MHz) delta: 174.46 (1C, C=O), 161.94 (1C, C=N), 33.65 (C-H), 31.27 (C-H), 29.02 (C-H), 28.89 (C-H), 28.72 (C-H), 28.69 (C-H), 28.53 (C-H), 24.48 (C-H), 22.07 (C-H), 13.92 (C-H); Anal. Cald. For C17H34N4O: C,65.76; H, 11.04; N, 18.05; Found: C, 65.70; H, 11.10; N, 17.05. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With acetic acid; In ethanol; under 760.051 Torr; for 3h;Reflux; | 0.259 g of 7-diethylamino-3- acetylcoumarin was dissolved in 10 mL of absolute ethanol, and then 0.09 g of carbazide was added, then added two drops of Acetic acid for catalysis, the mixture was stirred under reflux at normal pressure for 3 hours. After cooling to room temperature, a large amount of solid was precipitated and filtered under reduced pressure. The filter residue was washed with absolute ethanol to give a yellow solid, which is the target product based on the coumarin carbazone derivative. The yield of the target product was 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sulfuric acid; In ethanol; for 4h;Reflux; | General procedure: In 20 mL of absolute ethanol, thio<strong>[497-18-7]carbohydrazide</strong>/<strong>[497-18-7]carbohydrazide</strong>(0.01 mol) and 5-substituted isatins (0.01 mol) were stirred in the presence of H2SO4 (two drops). The reaction mixture was refluxed for 4h. The solid products so formed were filtered and washed with hot ethanol and dried (Scheme 1). They were prepared with minor modifications according to a reported procedure [13]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sulfuric acid; In ethanol; for 4h;Reflux; | General procedure: In 20 mL of absolute ethanol, thio<strong>[497-18-7]carbohydrazide</strong>/<strong>[497-18-7]carbohydrazide</strong>(0.01 mol) and 5-substituted isatins (0.01 mol) were stirred in the presence of H2SO4 (two drops). The reaction mixture was refluxed for 4h. The solid products so formed were filtered and washed with hot ethanol and dried (Scheme 1). They were prepared with minor modifications according to a reported procedure [13]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sulfuric acid; In ethanol; for 4h;Reflux; | General procedure: In 20 mL of absolute ethanol, thio<strong>[497-18-7]carbohydrazide</strong>/<strong>[497-18-7]carbohydrazide</strong>(0.01 mol) and 5-substituted isatins (0.01 mol) were stirred in the presence of H2SO4 (two drops). The reaction mixture was refluxed for 4h. The solid products so formed were filtered and washed with hot ethanol and dried (Scheme 1). They were prepared with minor modifications according to a reported procedure [13]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With acetic acid; In ethanol; for 5h;Reflux; | General procedure: Thio/<strong>[497-18-7]carbohydrazide</strong> (5.0 mmol) and terephthalaldehyde (2.5 mmol) with a few drops CH3 COOH as a catalyst, in an ethanol mixture (40 mL), were mixed and refluxed for 5 h. After the reaction was finished, the hot mixture was filtered. Then the filtrate was washed with ethanol. The formed solid was isolated and dried (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In water; at 20 - 80℃; | Dissolve the appropriate amount of <strong>[497-18-7]carbohydrazide</strong> in a mixed solvent of 10-50 mL of organic solvent and water to completely dissolve the <strong>[497-18-7]carbohydrazide</strong>, and then slowly add 4-methoxysalicylic aldehyde through a constant pressure dropping funnel In this solution, the reaction temperature is controlled to be 20-80 C. During this process, the dropping rate is strictly controlled. At the same time, the thin layer chromatography (TLC) spot plate is used to monitor the reaction to the end. Ultrasonic wash with deionized water 2 ~ 3 times, then wash with cold ethanol 2 ~ 3 times, wait until the intermediate.The product obtained in step 1 is a white powder with a yield of about 85% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In water; at 20 - 80℃; | Dissolve the appropriate amount of <strong>[497-18-7]carbohydrazide</strong> in a mixed solvent of 10-50 mL of organic solvent and water to completely dissolve the <strong>[497-18-7]carbohydrazide</strong>, and then slowly add 5-methyl salicylaldehyde to the solution through a constant pressure dropping funnel In the solution, the reaction temperature is controlled to 20 ~ 80 , the drop rate is strictly controlled during this process, and the thin layer chromatography (TLC) spot plate is used to monitor the reaction to the end, and the vacuum filtration is performed to obtain a white solid, which is used Ultrasonic washing with deionized water 2-3 times, then ultrasonic washing with cold ethanol 2-3 times, wait until the intermediate.The product obtained in step 1 is a white powder with a yield of about 82% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | General procedure: Cyclothiomethylation of carbonic acid diamidesand dihydrazides with diamine and H2Sor Na2S·9H2O (general procedure). A glass reactorequipped with a magnetic stirrer and a gas-inlet tube wasloaded with diamine (2.5 mmol), carbonic acid diamideor dihydrazide (1 mmol), EtOH (5 mL), and RbNO3(0.2 mmol), and the mixture was stirred for 1 h at roomtemperature (~20C), after which gaseous H2S wasbubbled into the mixture under constant stirring for 1 huntil saturation (method a) or Na2S·9H2O (20 mmol)was added (method b). After 4-h stirring at 60C, compounds1 and 2 were fi ltered off, washed with hot water,and dried, and compounds 3 and 4 were extracted withchloroform and purifi ed by column chromatography onSiO2. 1,2,4,5-Tetrazinan-3-one (4). Yield 0.092 g(90%, method a), amorphous powder, mp 80-86C.IR spectrum, nu, cm-1: 33283253, 2924-2854, 1651,1537, 1462, 1367, 1176, 1022, 987, 745734. 1 NMRspectrum, delta, ppm: 4.30 br.s (2, CH2), 4.74 and 7.95 br.s(4, N). 13C NMR spectrum, delta, ppm: 67.27 (CH2),162.85 (C=O). MALDI TOF, m/z: 140.053 [M + K H]+, 159.073 [M + K + H2O]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.38% | With phosphoric acid; In ethanol; at 20℃; | Dissolve yellow solid 2.6989g (8mmol) and <strong>[497-18-7]carbohydrazide</strong> 0.3606g (4mmol) in absolute ethanol,Add 2 ~ 3 drops of concentrated phosphoric acid, stir the reaction at room temperature for 4 ~ 24h,The obtained orange-yellow solid was recrystallized from absolute ethanol to obtain 2.1032 g of enhanced azo-Salen Schiff base fluorescent probe with a yield of 72.38% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With microbial transglutaminase In aq. phosphate buffer; dimethyl sulfoxide Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With formic acid; for 2h;Reflux; | General procedure: To a stirred H2O (25 mL) suspension of the appropriateboronic acid-containing aldehyde (2.22 mmol) and 1 dropof formic acid was added an aqueous solution (5 mL) ofcarbohydrazide (100 mg, 1.11 mmol). Compound 7 wassynthesized using MeOH as the solvent. The reactionmixture was heated at reflux for 2 h, at which pointthe reaction was allowed to cool to room temperature(RT). The resulting precipitate was collected by suctionfiltration and washed with Et2O (2 × 10 mL) to afford thepentacyclic oxadiazadiborinanes as white or off-whitesolids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With formic acid for 2h; Reflux; | General procedure for the synthesis of pentacyclicoxadiazadiborinanes General procedure: To a stirred H2O (25 mL) suspension of the appropriateboronic acid-containing aldehyde (2.22 mmol) and 1 dropof formic acid was added an aqueous solution (5 mL) ofcarbohydrazide (100 mg, 1.11 mmol). Compound 7 wassynthesized using MeOH as the solvent. The reactionmixture was heated at reflux for 2 h, at which pointthe reaction was allowed to cool to room temperature(RT). The resulting precipitate was collected by suctionfiltration and washed with Et2O (2 × 10 mL) to afford thepentacyclic oxadiazadiborinanes as white or off-whitesolids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With formic acid for 2h; Reflux; | General procedure for the synthesis of pentacyclicoxadiazadiborinanes General procedure: To a stirred H2O (25 mL) suspension of the appropriateboronic acid-containing aldehyde (2.22 mmol) and 1 dropof formic acid was added an aqueous solution (5 mL) ofcarbohydrazide (100 mg, 1.11 mmol). Compound 7 wassynthesized using MeOH as the solvent. The reactionmixture was heated at reflux for 2 h, at which pointthe reaction was allowed to cool to room temperature(RT). The resulting precipitate was collected by suctionfiltration and washed with Et2O (2 × 10 mL) to afford thepentacyclic oxadiazadiborinanes as white or off-whitesolids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With formic acid In water for 2h; Reflux; | General procedure for the synthesis of pentacyclicoxadiazadiborinanes General procedure: To a stirred H2O (25 mL) suspension of the appropriateboronic acid-containing aldehyde (2.22 mmol) and 1 dropof formic acid was added an aqueous solution (5 mL) ofcarbohydrazide (100 mg, 1.11 mmol). Compound 7 wassynthesized using MeOH as the solvent. The reactionmixture was heated at reflux for 2 h, at which pointthe reaction was allowed to cool to room temperature(RT). The resulting precipitate was collected by suctionfiltration and washed with Et2O (2 × 10 mL) to afford thepentacyclic oxadiazadiborinanes as white or off-whitesolids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.8% | Stage #1: carbonodihydrazide With potassium carbonate In N,N-dimethyl-formamide Reflux; Stage #2: n-butyl isobutyrate In N,N-dimethyl-formamide at 140 - 145℃; for 5h; | 5 Put 100 mL of N,N-dimethylformamide into a 500 mL four-necked flask, start stirring, put 89.2 g (0.98 mol) carbohydrazide and 71.2 g (0.51 mol) potassium carbonate, and heat to reflux. 147.1g (1.01mol) of n-butyl isobutyrate was added dropwise at reflux temperature, and the addition was completed in about 2 hours. Incubate at 140-145°C for 3 hours. After the reaction is complete, the N,N-dimethylformamide is removed under negative pressure, and then 100mL of water is poured into it, cooled to 0°C for crystallization, filtered, and dried to obtain 109.1g of white solid, the target product, with a purity of 98.1% , The yield is 76.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.2% | Stage #1: carbonodihydrazide With potassium carbonate In ethanol Reflux; Stage #2: Ethyl isobutyrate In ethanol at 70 - 75℃; for 4h; | 1 Put 100mL ethanol into a 500mL four-neck flask, Turn on the stirring, put in 86.4g (0.95mol) carbohydrazide and 79.6g (0.57mol) potassium carbonate, and heat to reflux. Under reflux conditions, 115.0g (0.98mol) ethyl isobutyrate was added dropwise, and the addition was completed in about 1 hour. Incubate at 7075 for 3 hours, After the reaction is complete, 80ml of ethanol is removed, then 100ml of water is added to the reaction solution, the temperature is slowly reduced to 0°C for crystallization, and filtered After drying, 103.6 g of the target product was obtained as a white solid with a purity of 98.0%. The yield was 75.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.1% | Stage #1: carbonodihydrazide With lithium hydroxide In toluene Reflux; Stage #2: Methyl isobutyrate In toluene at 105 - 110℃; for 4h; | 2 Put 100 mL of toluene into a 500 mL four-necked flask, start stirring, put 86.4 g (0.95 mol) carbohydrazide and 26.4 g (1.09 mol) lithium hydroxide, and heat to reflux. 102.1g (0.99mol) methyl isobutyrate was added dropwise at reflux temperature, and the addition was completed in about 2 hours. Incubate at 105-110°C for 2 hours. After the reaction is complete, the toluene is removed under negative pressure, and then 100 mL of water is poured in, cooled to 0°C for crystallization, filtered, and dried to obtain 100.7 g of white solid, which is the target product, with a purity of 98.0% and a yield of 73.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.8% | Stage #1: carbonodihydrazide; isobutyric Acid With potassium carbonate In water at 60 - 65℃; for 5h; Stage #2: With sodium hydroxide In water at 60 - 65℃; for 3h; | 3; 4 Put 100mL water into a 500mL four-neck flask, turn on the stirring, put 84.6g (0.93mol) carbohydrazide and 86.3g (0.97mol) isobutyric acid, Raise the temperature to 6065, and keep it for 5 hours at this temperature, Then 40.0g (0.99mol) sodium hydroxide was put into the reaction solution, Continue to heat up to reflux and keep it for about 3 hours under reflux conditions, After the reaction is completed, slowly lower the temperature to 0°C to crystallize, filter, After drying, 100.6 g of the target product was obtained as a white solid with a purity of 98.3%. The yield was 74.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With glacial acetic acid In ethanol Reflux; | 2.1. General Procedure for the Synthesis of Bis-SchiffBases of Carbohydrazide (1-27) General procedure: Bis-Schiff bases of carbohydrazide (1-27) were synthesized by refluxing a mixture of carbohydrazide (2 mmol), and a variety of substituted benzaldehydes (4 mmol) in the presence of 3-4 drops of acetic acid using ethanol as solvent. Completion of the reaction was monitored by TLC (hexane:acetone). After completion of the reaction, the reaction mixture was allowed to cool at room temperature. The precipitate obtained was filtered, and washed with hexane, and dried to obtain pure compounds 1-27 in high yields. Crystallization from ethanol afforded pure products. The structures of synthetic compounds were established by 1H-NMR spectroscopy, EI mass spectrometry, and elemental analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.54% | With trifluoroacetic acid In ethanol at 80℃; for 3h; | 2.2. Synthesis of L1 and L2 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde (0.7112 g, 2 mmol), hydrazinecarboxamide (0.3345 g, 4.5 mmol) and ethanol (30 mL) were mixed in a 50 mL flask and add in three drops CF 3 COOH. Stirred at 80 C for 3 h and recrystallized from toluene to afforded L1 (0.6695 g, 81.54 %) as a yellow solid. 1 H NMR (400 MHz, DMSO-d6) 10.29 (s, 1H), 7.58 (d, J = 8.7 Hz, 2H), 7.39-7.26 (m, 7H), 7.13-7.03 (m, 6H), 6.97 (d, J = 8.7 Hz, 2H), 6.29 (s, 2H). 13 C NMR (100 MHz, DMSO- d 6 ) 156.77, 147.63, 147.24, 144.51, 138.34, 135.29, 130.64, 130.18, 127.72, 127.00, 124.90, 124.04, 123.56, 123.28. FT-IR (KBr, cm -1 ): 3462 (s), 1690 (s),1589 (s), 1489 (m), 1279 (m), 754 (w), 695 (m). ESI-MS m/z: calcd. for C 24 H 20 N 4 OS 412.1358, Found: 413.1420 [M + H] + ( Figs. S1, S3 ). |
Tags: 497-18-7 synthesis path| 497-18-7 SDS| 497-18-7 COA| 497-18-7 purity| 497-18-7 application| 497-18-7 NMR| 497-18-7 COA| 497-18-7 structure
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