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CAS No. : | 5351-17-7 | MDL No. : | |
Formula : | C7H9N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WPBZMCGPFHZRHJ-UHFFFAOYSA-N |
M.W : | 151.17 | Pubchem ID : | 21450 |
Synonyms : |
p-Aminobenzohydrazide;p-Aminobenzoic acid hydrazide;4-POBN;Myeloperoxidase Inhibitor 1;NSC 640;Myeloperoxidase Inhibitor I;4-ABAH;4-aminobenzoic acid hydrazide;4-Aminobenzhydrazide
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 41.74 |
TPSA : | 81.14 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) : | -7.75 cm/s |
Log Po/w (iLOGP) : | 0.76 |
Log Po/w (XLOGP3) : | -0.75 |
Log Po/w (WLOGP) : | -0.12 |
Log Po/w (MLOGP) : | 0.54 |
Log Po/w (SILICOS-IT) : | -0.52 |
Consensus Log Po/w : | -0.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.58 |
Solubility : | 40.1 mg/ml ; 0.265 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.48 |
Solubility : | 50.4 mg/ml ; 0.334 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.66 |
Solubility : | 3.29 mg/ml ; 0.0218 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P304+P340-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 |
---|---|---|
99% | 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). |
82% | With hydrazine hydrate; In ethanol; for 24h;Reflux; | Ether-4-amino benzoate (I) (5 g, 0.03mol) and hydrazine hydrate (8ml) dissolved inabsolute ethanol (12 ml), the mixture was been heated at reflux for 24 hours, white crystalswere obtained after cooling the solution to room temperature. Yield 82%, mp 221C.IR, mmax/cm1: 1620 (-CO-NH-), 3300 (-N-H- secondary).1-H NMR (DMSO-d6),3.21 (2 H, s, H-1), 5.13 (2 H, s, H-7?), 6.58-7.69 (4 H, dd, H-5, H-6), 9.11 (1 H, s, H-2).13-C NMR (DMSO-d6), 113.42 (2C, C-6), 122.11 (1C, C-4), 127.91 (2C, C-5), 152.31(1C, C-7), 167.25 (1C, C-3). |
77% | With hydrazine hydrate; In ethanol; for 8h;Reflux; | Ethyl-4-aminobenzoate (0.06mol, 9.9g) was dissolved in (30 mL) of hydrazine hydrate 80%, then absolute ethanol (25 mL) was added in a rounded bottom flask and refluxed for 8 hours. At the end of the reaction, as monitored by TLC, the mixture was cooled to room temperature (RT), the crystals formed, filtered and recrystallized from absolute EtOH. White crystals, Yield 77% , M. P. 222-225 C, IR(KBr),( , cm-1): 3271 and 3234 prim. (NH2) str, 3033 Ar(CH) str, 1626 (C=O) amide str, 1604(NH) bend ,1545 (C=C) str, 843 out of plain(C-Hbenz.) bend. |
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; In methanol; at 5 - 20℃; | General procedure: Amixture of ethyl esters (25 mmol, 3a-k) and methanol (20mL)was taken in 100 mLround bottom flask and cooled up to 5C. Hydrazine hydrate (80%, 0.05-0.07 mol) wasadded gradually to the reaction mixture and kept stirring for 4-6 h at room temperature.Some of the hydrazide products were formed at room temperature while some esters gotaltered on refluxing with continuous stirring. The reaction completion was monitored byTLC using n-hexane and ethyl acetate as solvent system. After completion of reaction, colddistilled water was added to acquire the precipitates. Precipitates of consequent aryl/aralkylacid hydrazides (3a-k) were filtered, washed with distilled water, and dried to follow thefurther reaction.17-19 | |
With hydrazine hydrate; In ethanol;Reflux; | General procedure: Hydrazide ligands (1-12) were synthesized by reportedmethod [28,29]. Ethylbenzoate (25 mmol) was dissolved inethanol (75 mL), and then hydrazine hydrate (100 mmol)was added and the mixture refluxed for 5 h. The solid obtainedwas washed with hexane to afford the hydrazide.Other ligands were prepared from their respective esters. Theanalytical data of benzohydrazide (1), M.P. 116 C; 2-fluorobenzohydrazide (2), M.P. 74 C; 2-methoxybenzohydrazide(3), M.P. 83 C; 2-aminobenzohydrazide (4), M.P.124 C; 4-phenylsemicarbazide (5), M.P. 125 C; 3-aminobenzohydrazide(6), M.P. 79C; 4-aminobenzohydrazide (7),M.P. 229 C; 3-methoxybenzohydrazide (8), M.P. 94 C; 3-fluorobenzohydrazide (9), M.P. 138 C; 3-iodobenzohydrazide(10), M.P. 141 C; 4-iodobenzohydrazide (11) M.P.170 C and 3-bromobenzohydrazide (12) M.P. 160 C; werereported previously [28,30]. | |
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. | |
With hydrazine hydrate; In ethanol;Reflux; | General procedure: Ethyl ester (Va-n) (0.04 mol) was refluxed with 80% N2H4 · H2O(7.2 mL) for 3-4 h in 20 mL EtOH in a round-bottom flask (100 mL). The reaction was monitored by TLC. At completion, excess ice-cold distilled water (60 mL) was added to get the precipitate, which was filtered, washed with distilled water, and dried to acquire title compounds (VIa-n) [18, 19]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrazine hydrate; In ethanol; at 78℃; for 5h;Inert atmosphere; | 2.0g (13.2mmol) of 4-aminobenzoate was dissolved in 20mL of absolute ethanol, 1.0mL (19.8mmol) of hydrazine hydrate was dropwise added under N2 atmosphere, then the mixture was heated to 78C under reflux for 5h. After the solution was cooled to room temperature, the crude product was obtained by filtering and washing with deionized water, which was then recrystallized in ethanol. Yield (after recrystallization): 1.6g (80%). FTIR (wavenumber, cm-1): nuN-H, 3430, 3342, 3323, and 3230; nuC=O, 1670. 1H NMR (600MHz, 298K, DMSO-d6): delta (ppm), 9.43 (s, 1H), 7.63 (d, 2H), 5.62 (s, 2H), 4.43 (s, 2H). 13C NMR (150MHz, 298K, DMSO-d6): delta (ppm), 167.68, 152.53, 129.74, 121.10, and 113.94. |
71% | With hydrazine; at 70℃; for 12h;Inert atmosphere; | Methyl 4-aminobenzoate (2.0 g, 13.2 mmol) was added to a 10 mL round bottom flask with stir bar, followed by addition of anhydrous hydrazine (2.0 mL, 63.7 mmol). The reaction was then heated to 70C under N2 for 12 hours. After cooling, the mixture was poured into deionized water (100 mL), and the resulting precipitate was filtered and rinsed with additional water (100 mL) to give the product as a white solid(1.42 g, 71%). ?HNMR (400 MHz; DMSO-d6) 5= 9.26 (s, 1H), 7.54 (d, J= 8.6 Hz, 2H), 6.52(d, J 8.6 Hz, 2H), 5.57 (s, 2H), 4.26 (br s, 2H). ?3C NIVIR (100 MHz; DMSO-d6) 5= 166.4,151.5, 128.4, 119.9, 112.6. (ESI) m/z calcd for C7H,0N30 ([M+H]), 152.0818, found152. 08 14. |
45 g | With hydrazine hydrate; for 1h;Reflux; | General procedure: Compound I (45 g) was added in batches to a solution of 450 mL of hydrazine hydrate. The mixture was heated to reflux for 1 h and was monitored by TLC. After cooling to r.t., the excess hydrazine hydrate was evaporated under reduced pressure. The residue was poured into 50 mL of methanol, and the white solid compound III was filtered and dried to afford 45 g.KOH (22 g) was added at 0 C to a stirred solution of compound III (30 g) in anhydrous ethanol (400 mL) and DMF (50 mL). The reaction mixture was stirred for 10 min under N2. To this mixture, CS2 (45 g) was added dropwise at 0 C. The mixture was warmed to ambient temperature for 0.5 h and heated to reflux overnight until no starting material remained. The pH was adjusted to pH 4 with 2 N HCl, and the solid was filtered and dried to afford 19 g of yellow solid compound IV.To a stirred solution of compound IV (6.1 g) in acetone (40 mL), sulphur phosgene (2.9 mL) in acetone (11 mL) and saturated NaHCO3 were added dropwise simultaneously at 0 C. The mixture was then warmed to ambient temperature for 0.5 h. The mixture was poured into water to quench the reaction. The reaction was extracted with EtOAc, and the combined solution was dried with Na2SO4, filtered and evaporated under reduced pressure to give 5.7 g of yellow solid compound V.Compound V (100 g) was suspended in toluene (1000 mL), and hydrazine hydrate (42.5 mL) was slowly added. The mixture was stirred at r.t. under N2 until no starting material remained. The organic layer was separated, and the solid was filtered and washed with ethanol to afford 60 g of white solid compound 1, Stemazole.Total yield 14.6%, 1H NMR (400 MHz, DMSO-d6): delta 5.002 (s, 1H), 7.056 (s, 3H), 7.727 (d, J = 8.40 Hz, 2H), 7.871(d, 2H), 9.285 (S, 1H); 13C NMR (100 MHz, DMSO-d6): delta 179.44, 179.05, 160.68 (2C), 140.34 (2C), 124.73, 123.14, 121.01; HRMS (ESI) found: 268.0331, [C9H9N5OS2 + H]+ calcd: 268.0327. |
With hydrazine hydrate; In methanol;Reflux; | General procedure: Methyl benzoates were synthesized from their respective p-substituted benzoic acids, using excess dry methanol in the presence of H2SO4. para-Substituted benzoic hydrazides (2a-i) were prepared by reaction of the corresponding methyl benzoates (10 mmol) with hydrazine hydrate 99% (50 mmol) in methanol under reflux for 4-6 h. The excess solvent was removed under vacuum and the residue was filtered under suction, washed with water, and dried. The spectral and analytical data of benzoic hydrazide (2a) [26], 4-bromobenzoic hydrazide (2b) [27], 4-chlorobenzoic hydrazide (2c) [28], 4-fluorobenzoic hydrazide (2d) [26], 4-hydroxybenzoic hydrazide (2e) [29], 4-methoxybenzoic hydrazide (2f) [30], 4-methylbenzoic hydrazide (2g) [28], 4-nitrobenzoic hydrazide (2h) [28] and 4-aminobenzoic hydrazide (2i)[28] are in good agreement with literature values. | |
With hydrazine hydrate; In methanol;Reflux; | General procedure: Methyl benzoates were synthesized from their respective p-substituted benzoic acids, using excess of dry methanol in presence of H2SO4. p-Substituted benzoic acid hydrazides (2a-i) were prepared by reaction of the corresponding methyl benzoates (10 mmol) with hydrazine hydrate 99% (50 mmol) in methanol under reflux for 4-6 h. The excess solvent was removed under vacuum and the residue was filtered under suction, washed with water and dried. The spectral and analytical data of benzoic hydrazide (2a) [35], 4-bromobenzoic hydrazide (2b) [36], 4-chlorobenzoic hydrazide (2c) [37], 4-fluorobenzoic hydrazide (2d) [35], 4-hydroxybenzoic hydrazide (2e) [38], 4-methoxybenzoic hydrazide (2f) [39], 4-methylbenzoic hydrazide (2g) [37], 4-nitrobenzoic hydrazide (2h) [37] and 4-aminobenzoic hydrazide (2i) [38] are in good agreement with literature values. | |
With hydrazine hydrate; In ethanol; at 20 - 78℃; for 8h; | Step-2: A solution of 2.000 g (13.2 mmol) of methyl p-aminobenzoate dissolved in 20 ml of absolute ethanol was slowly added dropwise at room temperature with lml (19. 8 mmol) of 98% hydrazine hydrate at 78 C for 8 hours. A light yellow solution. Rotary Evaporator to evaporate the excessive amount of hydrazine hydrate and solvent to obtain white p-aminobenzohydrazide crude. A solution of 1.114 g (10.0 mmol) of p-aminobenzoyl hydrazide dissolved in 20 ml of absolute ethanol was slowly added dropwise to a three-necked flask under agitation. To three drops of triethylamine catalytic reaction, 78 (: reflux 0. 5h, the mixture cooled to room temperature available p-amino benzoyl salicylaldehyde hydrazone crude.Anhydrous ethanol recrystallization can be a number of pure products, filter was golden flake crystals. Dried and weighed. 4-amino salicylaldehyde benzoyl hydrazide hydrazone yield the highest yield of up to 86% | |
With hydrazine hydrate; In ethanol;Reflux; | Example 1: 2g (13.2mmol) of methyl anthranilate were dissolved in 20ml of absolute ethanol was slowly added dropwise 1ml (19.8mmol) 98% hydrazine hydrate, refluxed for 3-4h, rotary evaporation rotary evaporator, the solvent and excess hydrazine hydrate was distilled off to give a white solid crude amino-benzoyl hydrazine, taking 1.6g (10.5mmol) amino-benzoyl hydrazide was dissolved in absolute ethanol and 1.3ml (11mmol) 98% salicylaldehyde was slowly added dropwise three-neck flask, heated to reflux of 1-2h, cooled to give 4-amino benzoic acid hydrazide salicylaldehyde hydrazone crude product was recrystallized from ethanol several pure product by filtration, to give golden yellow flaky crystals, yield 86%. | |
With hydrazine hydrate; In ethanol; at 78℃; for 3h; | Dissolving methyl p-aminobenzoate in absolute ethanol,Excess hydrazine hydrate (98 wt%) was added dropwise,The reaction was heated at 78 C for 3 h.Rotary evaporation to remove solvent and unreacted hydrated hydrazine,The crude product p-aminobenzoic acid hydrazide is obtained.Thereafter, multiple ethanol recrystallizations were carried out.The product is then dissolved in an anhydrous ethanol solvent.Add a slight excess of salicylaldehyde,Heated back to reflux for 6 h,Cooling system,filter,The product is recrystallized from ethanol several times.dry,Salicylaldehyde-4-aminobenzoyl hydrazide; | |
With hydrazine hydrate; In ethanol; at 80℃; for 5h; | Dissolving methyl p-aminobenzoate in absolute ethanol and adding excess hydrazine hydrate (98 wt%).The mixture was heated to reflux at 80 C for 5 h, and the solvent and unreacted hydrazine hydrate were removed by rotary evaporation.The crude product p-aminobenzoyl hydrazide was obtained, followed by multiple ethanol recrystallization.The product is then dissolved in an anhydrous ethanol solvent and a slight excess of salicylaldehyde (98 wt%) is added dropwise.Heated to reflux for 5 h, cooled the system, filtered, and the product was recrystallized from ethanol several times.Dry to obtain salicylaldehyde-4-aminobenzoyl hydrazide; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With triethylamine; In ethanol; at 78℃; for 0.5h; | Step-2: A solution of 2.000 g (13.2 mmol) of methyl p-aminobenzoate dissolved in 20 ml of absolute ethanol was slowly added dropwise at room temperature with lml (19. 8 mmol) of 98% hydrazine hydrate at 78 C for 8 hours. A light yellow solution. Rotary Evaporator to evaporate the excessive amount of hydrazine hydrate and solvent to obtain white p-aminobenzohydrazide crude. A solution of 1.114 g (10.0 mmol) of p-aminobenzoyl hydrazide dissolved in 20 ml of absolute ethanol was slowly added dropwise to a three-necked flask under agitation. To three drops of triethylamine catalytic reaction, 78 (: reflux 0. 5h, the mixture cooled to room temperature available p-amino benzoyl salicylaldehyde hydrazone crude.Anhydrous ethanol recrystallization can be a number of pure products, filter was golden flake crystals. Dried and weighed. 4-amino salicylaldehyde benzoyl hydrazide hydrazone yield the highest yield of up to 86% |
86% | In ethanol;Reflux; | Example 1; 2g (13.2mmol) of methyl anthranilate were dissolved in 20ml of absolute ethanol was slowly added dropwise 1ml (19.8mmol) 98% hydrazine hydrate, refluxed for 3-4h, rotary evaporation rotary evaporator, the solvent and excess hydrazine hydrate was distilled off to give a white solid crude amino-benzoyl hydrazine, taking 1.6g (10.5mmol) amino-benzoyl hydrazide was dissolved in absolute ethanol and 1.3ml (11mmol) 98% salicylaldehyde was slowly added dropwise three-neck flask, heated to reflux of 1-2h, cooled to give 4-amino benzoic acid hydrazide salicylaldehyde hydrazone crude product was recrystallized from ethanol several pure product by filtration, to give golden yellow flaky crystals, yield 86%. |
In ethanol; for 6h;Reflux; | Dissolving methyl p-aminobenzoate in absolute ethanol,Excess hydrazine hydrate (98 wt%) was added dropwise,The reaction was heated at 78 C for 3 h.Rotary evaporation to remove solvent and unreacted hydrated hydrazine,The crude product p-aminobenzoic acid hydrazide is obtained.Thereafter, multiple ethanol recrystallizations were carried out.The product is then dissolved in an anhydrous ethanol solvent.Add a slight excess of salicylaldehyde,Heated back to reflux for 6 h,Cooling system,filter,The product is recrystallized from ethanol several times.dry,Salicylaldehyde-4-aminobenzoyl hydrazide; |
In ethanol; for 5h;Reflux; | Dissolving methyl p-aminobenzoate in absolute ethanol and adding excess hydrazine hydrate (98 wt%).The mixture was heated to reflux at 80 C for 5 h, and the solvent and unreacted hydrazine hydrate were removed by rotary evaporation.The crude product p-aminobenzoyl hydrazide was obtained, followed by multiple ethanol recrystallization.The product is then dissolved in an anhydrous ethanol solvent and a slight excess of salicylaldehyde (98 wt%) is added dropwise.Heated to reflux for 5 h, cooled the system, filtered, and the product was recrystallized from ethanol several times.Dry to obtain salicylaldehyde-4-aminobenzoyl hydrazide; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol; at 80℃; for 3h;Inert atmosphere; | First, 1.6g (10.5mmol) of <strong>[5351-17-7]4-aminobenzohydrazide</strong> (SH), 1.3mL (11.0mmol) of salicylaldehyde and 30mL of ethanol were added to a 100mL three-neck bottle. The mixture solution was stirred at 80C for 3h. After cooling to room temperature, a pale-yellow precipitate was obtained, which was then washed with a small amount of cool ethanol. Yield: 86.0%. FTIR (wavenumber, cm-1): nuOH, NH, 3455, 3356, and 3281; nuC=O, 1664. 1H NMR (600MHz, 298K, DMSO-d6), delta (ppm), 12.65 (s, 1H), 9.01 (s, 1H), 7.72 (d, 2H), 7.54 (dd, 1H), 5.76 (s, 1H). 13C NMR (150MHz, 298K, DMSO-d6), delta (ppm), 163.50, 158.32, 153.50, 147.81, 131.80, 130.62, 130.32, 120.11, 119.67, 119.64, 117.30, and 113.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; at 80℃; for 12h;Inert atmosphere; | (1) 0.45 g (3 mmol) of p-aminobenzoic acid hydrazide was placed in a 100 mL three-necked flask, and then 50 mL of absolute ethanol was added to the three-necked flask.Stir it thoroughly to dissolve it, under a nitrogen atmosphere,0.43 g (3.2 mmol) of phenyl isothiocyanate was slowly added dropwise, and the temperature was raised to 80 C.Reaction for 12 h, then cooled to room temperature and rotary evaporation to remove excess solventRecrystallization from absolute ethanol gave a pale yellow solid, which gave product 1,The yield was 80%. |
53% | In ethanol; for 1.5h;Inert atmosphere; Reflux; | 1.6 g (10.6 mmol) of p-aminobenzoic acid hydrazide was dissolved in 30 mL of ethanol, dissolved under heating with nitrogen and dissolved.0.47 mL (11.0 mmol) of phenyl isothiocyanate was slowly added dropwise. The mixture was refluxed for 1.5 h to give a pale yellow solution, and the mixture was cooled to room temperature to precipitate a large white solid. Pure ethanol can be obtained by recrystallization of absolute ethanol.Filtered to give a white powdery solid.The intermediate probe was obtained in a yield of 53%. |
In ethanol;Reflux; | General procedure: 4-Aminobenzohydrazide (5 g, 0.041 mol) and appropriate 4-substituted phenylisocyanate derivatives (0.041 mol) were refluxed in ethanol (100 mL) for 2-4 h. After TLC screening, reaction mixture was filtered and recrystallized from ethanol. |
In ethanol; for 10h;Reflux; Inert atmosphere; | Take a 100 mL three-necked flask.Weigh 0.151g (1.0mmol) of p-aminobenzohydrazide20mL in ethanol solution,The mixture was dissolved by heating under a nitrogen atmosphere and slowly slowly added to the phenyl isothiocyanate 0.135 g (1.0 mmol).Heated to reflux for 10 h until the solution was a pale yellow solution.The mixture was cooled to room temperature to precipitate a large white solid which was filtered.Pure ethanol can be obtained by recrystallization of absolute ethanol.Filtering to obtain a white powdery solid A,That is, 4-phenylthiosemicarbazide; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | 4-Aminobenzohydrazide(1) (0.02 mol,3.0 g) dissolved in absolute EtOH (20 mL) , and cooled to 20 C in the ice bath. Then after addition of potassium hydroxide (KOH) to the mixture, (0.027 mol,1.5 g) in an absolute EtOH (10 mL), and stirred for 15 min. Then CS2 (0.024 mol, 1.5 mL) was added gradually. The reaction was refluxed for12 hours. The solvent was reduced by rotary evaporator, and the produced solid was dissolved in (25 mL) of cold D.W and distilled water and acidified with 10% HCl, until precipitation of light yellow crystals of (3), obtained and recrystallized from absolute EtOH. Light yellow crystals, Yield 64%, M.P 243-245 C, IR(KBr),(nu, cm-1): 3315 and 3220 cm-1 prim (NH2) str, 3059 cm-1 Ar(CH) str, 2557 cm-1 str of (SH) thiol gr.,1618 cm-1 (NH) bend., 1603 cm-1 (C=N) str, 1570, 1512 and 1485 cm-1 (C=C)str, 1271 cm-1 asym (C-O-C) str ,1065 cm-1 sym (C-O-C) str, 829 cm-1 (out of plain C-Hbenz.)bend.; 1H NMR(300 MHz, DMSO-d6, delta=ppm): 7.48 (d, 2H, 2Ar-H), 6.60(d, 2H, 2Ar-H), 5, 90(brs,1H,SH), 7.78 (s, 2H,NH2). | |
63.9% | With potassium hydroxide; In ethanol; water; for 15h;Reflux; | General procedure: A solution of compounds 3(a-f) (1 mmol) and CS2/KOH (1 mmol) was taken in a mixture of ethanol/water in 1:1ratio and refluxed for 15 h. With the help of TLC taking hexane: ethyl acetate (7.5:2.5) as mobile phase, the synthesis of reaction mixture had monitored. After reaction undergoes completion, its volume had reduced under pressure to half of its original volume. The reaction mixture was diluted with cold water and acidified with conc. HCl that resulted in the formation of solid precipitation. The product was filtered and the resulting precipitate was washed with water. Recrystallization was performed using methanol: dichloromethane (8:2) to obtain the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | (3 g, 0.02 mol) of the product (II) was dissolved in absolute ethanol (30 ml) at atemperature of (0C), potassium hydroxide (1.2 g, 0.027 mol) dissolved in the minimumof distilled water, was added. After stirring for 15 min (1.21 ml, 0.02 mol) of carbondisulfide was added, the solution was heated at reflux for 14 hours. The solvent wasremoved using a rotary evaporator. A yellow precipitate was formed after the additionof cold distilled water (25 ml), and HCl 10% (10 ml). Yield 88%, mp 238C.IR, mmax/cm1: 2770 (-S-H), 1114.6 (C-O, oxadiazole), 1685 (-CN aromatic),3349.7, 3424.9 (-NH2). 1-H NMR (DMSO-d6), 5.47 (2 H, s, H-7?), 2.68 (1H, H-1), 6.98-7.86 (4 H; dd, H-5, H-6). 13-C NMR (DMSO-d6), 110.8 (1C, C-4), 114.32 (2C, C-6),126.44 (2C, C-5), 154.1 (1C, C-7), 162.66 (1C, C-3), 175.48 (1C, C-2). | |
19 g | General procedure: Compound I (45 g) was added in batches to a solution of 450 mL of hydrazine hydrate. The mixture was heated to reflux for 1 h and was monitored by TLC. After cooling to r.t., the excess hydrazine hydrate was evaporated under reduced pressure. The residue was poured into 50 mL of methanol, and the white solid compound III was filtered and dried to afford 45 g.KOH (22 g) was added at 0 C to a stirred solution of compound III (30 g) in anhydrous ethanol (400 mL) and DMF (50 mL). The reaction mixture was stirred for 10 min under N2. To this mixture, CS2 (45 g) was added dropwise at 0 C. The mixture was warmed to ambient temperature for 0.5 h and heated to reflux overnight until no starting material remained. The pH was adjusted to pH 4 with 2 N HCl, and the solid was filtered and dried to afford 19 g of yellow solid compound IV.To a stirred solution of compound IV (6.1 g) in acetone (40 mL), sulphur phosgene (2.9 mL) in acetone (11 mL) and saturated NaHCO3 were added dropwise simultaneously at 0 C. The mixture was then warmed to ambient temperature for 0.5 h. The mixture was poured into water to quench the reaction. The reaction was extracted with EtOAc, and the combined solution was dried with Na2SO4, filtered and evaporated under reduced pressure to give 5.7 g of yellow solid compound V.Compound V (100 g) was suspended in toluene (1000 mL), and hydrazine hydrate (42.5 mL) was slowly added. The mixture was stirred at r.t. under N2 until no starting material remained. The organic layer was separated, and the solid was filtered and washed with ethanol to afford 60 g of white solid compound 1, Stemazole.Total yield 14.6%, 1H NMR (400 MHz, DMSO-d6): delta 5.002 (s, 1H), 7.056 (s, 3H), 7.727 (d, J = 8.40 Hz, 2H), 7.871(d, 2H), 9.285 (S, 1H); 13C NMR (100 MHz, DMSO-d6): delta 179.44, 179.05, 160.68 (2C), 140.34 (2C), 124.73, 123.14, 121.01; HRMS (ESI) found: 268.0331, [C9H9N5OS2 + H]+ calcd: 268.0327. | |
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. |
Example 1 The preparation of 4-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) thiosemicarbazide (Ia) Scheme I: 0.76 g (0.005M) p-Aminobenzoylhydrazide (2) is dissolved in 30 ml methanol. KOH aqueous solution (0.005M), CS2 0.3 ml (0.005M) are added, and the mixture is heated to reflux. After 24 h, methanol is removed by rotary evaporation. About 30 ml water is added, the resultant solution is acidified with 6N HCl, filtrated under vacuum, washed with ethyl ether, and dried to obtain the product 2-thiol-5-p-aminophenyl-1,3,4-oxadiazole (3); Compound 3 (579 mg) is dissolved in 20 ml methanol. KOH 168 mg and CS2 0.2 ml are added. The reaction takes place at room temperature for 4 hours. The mixture is filtrated, and methanol is removed by rotary evaporation under vacuum. Tetrahydrofuran (10 ml), toluene sulfonyl chloride (266 mg) are added. After reacting at room temperature for 1 hour, hydrazine hydrate (0.19 ml) is added. The reaction takes places at room temperature overnight. The mixture is filtrated under vacuum, recrystallized with ethanol, and dried to obtain a product (160 mg, 20% yield) IR v (liquid paraffin) cm-1: 3320, 3212, 1810, 1596, 1292. | ||
With potassium phosphate; In water; at 20℃;Reflux; | General procedure: A mixture of the corresponding acylhydrazine (3 mmol), potassium phosphate (1.02 g, 3 mmol), and carbon disulfide (0.23 g, 3 mmol) in water (15 mL) was stirred at rt for 10 min. After refluxing for an additional 2-3 h, propylene oxide (0.18 g, 3 mmol) was added. Stirring was continued at rt until the intermediate convert completely (monitored by TLC, about 0.5-1 h), the mixture was extracted with EtOAc (3×10 mL). The combined organic layer was washed with water and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization or silica gel column to afford the corresponding product 10a-l. | |
With potassium hydroxide; In ethanol;Reflux; | General procedure: The aryl/aralkyl acid hydrazides (0.01 mol, 3a-k) were dissolved in ethanol(35-40 mL) followed by the addition of KOH (0.03 mol) and CS2 (0.01 mol) in 250 mLround bottom flask fitted with a reflux condenser. The reaction mixture was refluxedfor 3-6 h along with proper stirring and the progress of reaction was monitored byTLC. After completion of reaction, the reaction mixture was diluted with distilled H2O(70-75 mL) and acidified with dilute HCl (pH 2-3) to convert salt of oxadiazole into acidicform. Precipitates of corresponding 5-substituted-1,3,4-oxadiazole-2-thiols (4a-k) werefiltered, washed with distilled water, and dried. To get the pure product, precipitates wererecrystallized from methanol.17-19 | |
With hydrazine hydrate; potassium hydroxide; In ethanol;Reflux; | General procedure: Solid KOH (0.03 mol) was dissolved in 25 mL EtOH on reflux in a 100 mL round-bottom flask. (Un)Substituted-benzohydrazide (VIa-n) (0.03 mol) was refluxed with CS2 (0.06 mol) in this basified EtOH for 5-6 h. The reaction was monitored by TLC. At completion, excess ice-cold distilled water (60 mL) wasadded to form homogeneous solution. pH was adjusted to 5-6 by pouring dilute HCl; precipitatethus formed was filtered, washed with distilled water and dried. The formed products (VIIa-n) were also re-crystallized from EtOH [18, 19]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium In methanol | 28 3-(p-AMINOPHENYL)-5-(4-PYRIDYL)-1,2,4-TRIAZOLE EXAMPLE 28 3-(p-AMINOPHENYL)-5-(4-PYRIDYL)-1,2,4-TRIAZOLE To 4-cyanopyridine (4.2 g.) in methanol (60 ml.) is added sodium (0.2 g.). The solution is allowed to stand for 0.5 hour at room temperature and is then added to a suspension of p-aminobenzhydrazide (6.4 g.) in 150 ml. of methanol. The resulting solution is heated 20 hours at reflux during which time a solid separates. The solid is filtered and heated to 245° C. over 1 hour and maintained at that temperature for an additional 15 minutes. After cooling the solid is recrystallized from a mixture of acetonitrile and water to yield 3-(p-aminophenyl)-5-(4-pyridyl)-1,2,4-triazole (2 g.) m.p. 251°-252.5° C. Analysis calculated for C13 H11 N5. Calculated: C,65.81; H,4.67; N,29.52. Found: C,65.95; H,4.71; N,29.61. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.7% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 48h; | To a solution of 2-(4-fluorophenoxy)nicotinic acid ( 600 mg, 2.57 mmole) in 30 ml methylene chloride was added DMAP (628 mg, 5.15 mmole), EDCI (988 mg, 5.15 mmole) and 4-aminobenzoic hydrazide (427 mg, 2.83 mmole). The reaction mixture was stirred at rt for 2 days. The mixture was filtered off, the solid was washed with 10 ml methylenechloride and dried to give 770 mg product, 81.7% yield. HNMR |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.3% | In tetrahydrofuran;Reflux; | General procedure: Tripod (1) (0.106 g, 0.24 mmol) was added to a solution of benzoic hydrazide (2a) (0.109 g, 0.8 mmol) in tetrahydrofuran (75 mL) and the reaction mixture was stirred under reflux for 15-18 h. The solvent was removed by evaporation under reduced pressure. The residue was filtered under suction and washed several times withhot tetrahydrofuran. The resulting solid (3a) was dried in vacuo at 40 C for 4 h. The same general procedure was followed for the compounds 3b-i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With nickel(II) nitrate hexahydrate; In ethanol; at 20℃; | General procedure: 1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanone 3 (1.0 mol), benzohydrazide 4a-h (1.25 mol), and Ni(NO3)2 · 6H2O (10 mol%) were mixed together in ethanol (7 mL) and stirred at room temperature for 1-2 h. After the completion of reaction (checked by TLC), the solid separated was filtered, washed well with ethanol (5 mL) and water (10 mL), and finally dried and recrystallized from ethanol to get the pure solid sample 5a-h. Physical, analytic, and spectroscopic characterization data of the compounds 5a-h are presented hereafter. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol at 100℃; for 0.166667h; Microwave irradiation; | MicrowaveMethod for the Synthesis of (3a-3n) General procedure: Amultimodereactor (Synthos 3000 Anton Paar, GmbH, 1400Wmaximum magnetron) was used. The initial step was conductedwith 4-Teflon vessels rotor (MF 100) that allowsthe reactions to process under the same conditions. Isatinderivatives 1a-1f and hydrazine hydrate 2a, thiosemicarbazide2b, or 4-aminobenzamide 2c were mixed together ina small portion of ethanol and then subjected to microwaveirradiation (400 watt). The vessels were heated for 5 min at100∘C and held at the same temperature for another 5min.cooling was accomplished by a fan (5 min).The final productwas washed with cold ethanol and then dried under vacuumto afford the products 3a-3n in high yield and purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | 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 |
---|---|---|
77.03% | In ethanol; for 2h;Reflux; | General procedure: The target compounds (2a-2e)-(6a-6f) were synthesized by reacting equimolar proportion of substituted benzhydrazides and benzenesulfonyl hydrazide with 5-substituted 2-furan carboxaldehyde in ethanol absolute under reflux for 2 h. Compounds [(7a-7e)-(8b-8e)] were synthesized by replacing the furan ring with thiophene and pyrrole. The compounds [(9a-9f)- 10a-10f)] were also prepared from the reaction of furoic hydrazide and the corresponding hydrazide of thiophene with a variety of aromatic aldehydes, furan-2-carboxaldehyde and thiophene-2-carboxaldehyde in ethanol absolute ethanol under reflux for 2 h. The progress of the reaction was monitor by TLC. The insoluble product was filtered off |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: A EtOH (40 mL) solution of o-aminobenzoyl hydrazine (1a) (1.51 g, 10 mmol) was added to a suspension of 1,3-dimethyl-5-acetyl barbituric acid (1b) (1.98 g, 10 mmol) in EtOH (40 mL) at room temperature. After stirring for 5 min at the same temperature, catalytic amount glacial acetic acid was added to the reaction mixture and refluxed for 12 h. Then the mixture was allowed to cool down to room temperature and the white solid precipitate collected. Recrystallization from DMSO gave white crystals. (2.4 g, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.4% | With acetic acid; In ethanol; at 20℃; for 3h; | 0.5mmol1- [4- hydroxy-3- (2-methyl-benzofuran-5-yl) phenyl] -2-propanone, 0.55mmol4- aminobenzoyl hydrazide, dissolved with 20ml of ethanol was added 0.2ml of glacial acetic acid , after stirring at room temperature for 3h, add 50ml ethanol distilled under reduced pressure to a residual solution 5ml, TLC monitoring completion of the reaction; adding water, fully shock, standing, the precipitated solid was filtered, the filter cake washed with water and washed with 50% ethanol and dried to give a pale yellow mg of 1- [4-hydroxy-3- (2-methyl-benzofuran-5-yl) phenyl] -4-amino-benzoyl-2-propanone hydrazone, yield 71.4% |
71% | With acetic acid; In ethanol; for 5h;Reflux; | General procedure: To a solution of 5 (0.5 mmol) and substituted benzoylhydrazide (0.55 mmol) in EtOH(20 ml) acetic acid (0.2 ml) was added. After stirred and refluxed for 5 h, the reactionwas concentrated, poured into saturated salt water, shocked, and placed until precipitation.Then the precipitate was separated by filtration, washed with water, and driedto afford substituted benzoylhydrazone (7-23). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | 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 |
---|---|---|
With toluene-4-sulfonic acid; In dimethyl sulfoxide; toluene; for 8h;Inert atmosphere; Reflux; Schlenk technique; | The reagents 1,4-di(2-thienyl)-1,4-butanedione and p-aminobenzoyl hydrazide are prepared according to the methods as given in the literature [31,32]. All experiments are carried out under dry argon by using Standard Schlenk techniques. Solvents are dried, distilled and saturated with argon. (0011) The monomer (HKCN) is synthesized from 1,4-di(2-thienyl)-1,4-butanedione and p-aminobenzoyl hydrazide in the presence of catalytically amount of p-toluenesulphonic acid (PTSA) [11]. A round-bottomed flask equipped with an argon inlet and magnetic stirrer is charged with 2.5g (10mmol) 1,4-di(2-thienyl)-1,4-butanedione, 1.51g (10mmol) p-aminobenzoyl hydrazide, 0.2g (1.2mmol) PTSA, 1ml DMSO and 20ml toluene. The resultant mixture is stirred and refluxed for 18h under argon. Darkened solution is filtered hot to remove oily decomposition products. Then, the mixture is cooled to room temperature and the solid product is filtered off to give a yellow powder that is washed with pentane (3×15ml) and air-dried, yield 3.1g%85, (mp 142-143C) [11]. The synthetic route of the monomer is shown in Scheme 1 . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With acetic acid; In methanol; for 12h;Reflux; | General procedure: Thiochroman-4-ones (0.5 mmol) were dissolved in anhydrous methanol (25 mL). The mixture was heated at reflux and then hydrazide (1.0 mmol, 2 equiv.) and glacial acetic acid 60 μL were added. After 12 h at reflux, the resulting precipitate was collected through filtration and washed with methanol. After drying under vacuum, the residue was passed through a small pad of silica gel with ethyl acetate, after evaporation of the solvent acyl hydrazones were obtained as white solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | 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 |
---|---|---|
82% | With cerium(III) chloride heptahydrate; In ethanol; at 65℃; | To a stirred suspension of compound 6 (0.50 mmol) and the appropriate hydrazide (0.50 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 1-2 h. Reaction?s completion was monitored by TLC, using appropriate eluent system. The reactional medium was allowed to reach room temperature, giving orange precipitates. After cooling, the solids were filtered off, and washed with cold ethanol. Recrystallization from ethanol afforded the samples for biological purposes, which were dried in an Abderhalden?s apparatus to remove traces of solvent. 4.1.5.1. N?-[(1E)-3-(N-methyl-4-nitrophenylhydrazono)]-(2E)-propan-2-ylidene-<strong>[5351-17-7]4-aminobenzohydrazide</strong> (SintMed75). Orange solid,yield 82%; mp 284.2-286.4 C; Rf 0.27 (AcOEt); IR (KBr, mmaxcm1): 3466, 3342, 3226 (NAH), 3022 (CAH Ar), 1642 (CO),1601 (CC), 1574 (CN); 1H NMR (400 MHz, DMSO-d6, d ppm):10.3 (s, 1H, CONH), 8.17 (d, 2H, 3J = 9.6 Hz, 4-NO2Ph H-3,5), 7.66(d, 2H, 3J = 8.8 Hz, 4-NH2Ph H-2,6), 7.63 (s, 1H, NCH), 7.55 (d,2H, 3J = 9.2 Hz, 4-NO2Ph H-2,6), 6.60 (d, 2H, 3J = 8.8 Hz, 4-NH2PhH-3,5), 5.79 (s, 2H, NH2), 3.51 (s, 3H, NCH3), 2.30 (s, 3H, CH3);13C NMR (100 MHz, DMSO-d6, d ppm): 163.7 (1C, CO), 152.3(1C, CH3CN), 151.6 (1C, 4-NH2Ph C-4), 151.3 (1C, 4-NO2Ph C-1),139.5 (1C, 4-NO2Ph C-4), 138.6 (1C, NCH), 129.8 (2C, 4-NH2PhC-2,6), 125.3 (2C, 4-NO2Ph C-3,5), 119.5 (1C, 4-NH2Ph C-1), 113.4(2C, 4-NO2Ph C-2,6), 112.4 (2C, 4-NH2Ph C-3,5), 32.7 (1C, NCH3),11.2 (1C, CH3); UHPLC-TOF-MS for C17H18N6O3 calcd (found)/Error:353.1363 (353.1362, [MH])/0.3 ppm; 355.1514 (355.1519, [M+H]+)/1.4 ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In methanol; at 50℃; for 3h;Inert atmosphere; | General procedure: The ligands L3, L4, L5 and L6 were synthesized using <strong>[65-22-5]pyridoxal hydrochloride</strong> (0.180g, 8mmol) solubilized in methanol (15mL). Then 4-hydroxybenzoic hydrazide (L3), 4-methoxybenzoic hydrazide (L4), 4-aminobenzoic hydrazide (L5), and 4-nitrobenzoic hydrazide (L6) were added (0.134g, 0.146g, 0.133g, 0.160g, 8mmol each, respectively). The reaction solution remained at 50C and constant stirring, with reaction time of 2h (L3-L4) and 3h (L5-L6). After this period, the reaction mixture was cooled to room temperature and the methanol was then evaporated under reduced pressure, whereby a yellow solid was obtained (Scheme 2 ). Thin-layer chromatography plates monitored the reactions (Hex/Ac 80-20). The synthetic route used to obtain the L4 ligand is similar to that proposed by K. Ramdasand and co-workers [29]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | To a solution of 4-aminobenzohydrazide (1.5 g,0.01 mol) and 1-Adamantane carboxylic acid (1.80 g, 0.01 mol) in DCM (50 mL)was added EDCI (2.86 g, 0.015 mol). The reaction was stirred at roomtemperature for 8 h, TLC showed consumption of the 4-aminobenzohydrazidestarting material and formation of the product. Solvent was removed in vacuo andthe residue was taken up in EtOAc (50 mL). This was washed with saturated aq.NaCl (50 mL) and then dried over MgSO4. Solvent was removed in vacuo to yieldthe crude product, which was then purified by flash column chromatography toafford the condensation product carbohydrazide (2.85 g, 91%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In butan-1-ol;Reflux; | General procedure: 4-Aminobenzohydrazide (2) was added to 1.1 equimolar amount of corresponding phenyl isothiocyanate (3a-3f) or phenyl iso- cyanate (4a-4f) solutions in 10 mL n-butanol (3a-3f) or chloro- form (4a-4f). The mixture was stirred at reflux conditions and then cooled to room temperature after the reaction was completed. Following the evaporation of the solvent under atmospheric pres- sure, the resulting precipitate was filtered offand washed with n- butanol (3a-3f) or chloroform (4a-4f). The solid residue was puri- fied by crystallization from ethanol to afford the target compounds (3a-3f, 4a-4f). |
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P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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