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CAS No. : | 1613-86-1 | MDL No. : | MFCD00465738 |
Formula : | C7H7N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 181.15 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
55% | boron trifluoride dimethyl etherate; In tetrahydrofuran; at 0 - 20℃; | Synthesis of 3-(4-Nitro-phenyl)-[1,2,4]oxadiazole Triethyl orthoformate (2.93 g, 19.8 mmol) was added to a stirred solution of <strong>[1613-86-1]N-hydroxy-4-nitro-benzamidine</strong> (1.2 g, 6.6 mmol) in THF (15 mL). The mixture was cooled to 0 C. and boron triflouride dimethyl ether (900 mg, 7.9 mmol) was added drop wise. The mixture was maintained at room temperature for three hours. The volatiles were evaporated and the residue was washed with ether and dried to afford 650 mg (55%) of 3-(4-nitro-phenyl)-[1,2,4]oxadiazole. |
55% | With boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; | Intermediate 58-Synthesis of 4-[1,2,4] Oxadiazol-3-yl-phenylamine To a stirred solution of 4-nitrobenzonitrile (1 g, 0.0068 mol) in ethanol (20 mL) and water (8 mL) was added hydroxylamine hydrochloride (1.9 g, 0.0272 mol) followed by sodium carbonate (2.2 g, 0.0204 mol). The resulting mixture was heated to reflux at 85 C. under an atmosphere of nitrogen for 2 hours The reaction was monitored by TLC (50% Ethyl acetate in Hexane). The volatiles were evaporated and the residue was extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to get afford 1.2 g (98%) of <strong>[1613-86-1]N-hydroxy-4-nitro-benzamidine</strong>. 1H NMR (DMSO-d6): delta 10.2 (s, 1H), 8.24 (d, 2H), 7.97 (d, 2H), 6.03 (s, 2H). To a stirred solution of <strong>[1613-86-1]N-hydroxy-4-nitro-benzamidine</strong> (1.2 g, 0.0066 mol) in THF (15 mL) was added triethyl orthoformate (2.93 g, 0.0198 mol). The resulting mixture was cooled to between 0 and 5 C. Boron trifluoride dimethyl ether (0.9 g, 0.0079 mol) was then added dropwise and the resulting mixture was stirred at ambient temperature for 3 hours. Volatiles were evaporated under reduced pressure and the resulting residue was washed with ether and dried to afford 0.65 g (55%) of 3-(4-nitro-phenyl)-[1, 2, 4]oxadiazole. To a stirred solution of 3-(4-nitro-phenyl)-[1, 2, 4]oxadiazole (0.2 g, 0.001 mol) in THF (15 mL) was added ammonium chloride (0.214 g, 0.004 mol) in water (5 mL) followed by zinc powder (0.262 g, 0.004 mol) portionwise. The resulting mixture was stirred at ambient temperature for 1 hr and then heated to 65 C. for 5 hours. The mixture was then filtered through celite and the organic layers were concentrated under reduced pressure. The residue was extracted with ethyl acetate. The organic layers were washed with brine solution, dried over Na2SO4 and evaporated under reduced pressure to afford 0.155 g (92%) of 4-[1, 2, 4]oxadiazol-3-yl-phenylamine. 1H NMR (DMSO-d6): delta 9.5 (s, 1H), 7.7 (d, 2H), 6.7 (d, 2H), 5.8 (s, 2H). |
for 24.0h;Heating / reflux; | Reference Example 24 3-(4-Nitrophenyl)[1,2,4]oxadiazole A mixture of <strong>[1613-86-1]N-hydroxy-4-nitrobenzamidine</strong> (1.0 g) and orthoformic acid triethyl ester (20 ml) was stirred under reflux for 24 hours. After cooling, the reaction mixture was concentrated under reduced pressure, and the thus obtained residue was washed with diisopropyl ether and ethanol and then collected by filtration and dried to obtain the title compound (520 mg) as a crystalline solid. 1H-NMR (400 MHz, CDCl3) delta: 8.28-8.45 (4H, m), 8.85 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 11.0h;Heating / reflux; | Reference Example 23 5-Methyl-3-(4-nitrophenyl)[1,2,4]oxadiazole A mixture of <strong>[1613-86-1]N-hydroxy-4-nitrobenzamidine</strong> (1.0 g) and acetic anhydride (30 ml) was stirred under reflux for 11 hours. After cooling, the reaction mixture was concentrated under reduced pressure, and to the thus obtained residue was added saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure, the thus obtained residue was purified by silica gel column chromatography, and the fraction obtained from the elude of dichloromethane:methanol = 100:1 was concentrated under reduced pressure to obtain the title compound (690 mg) as a crystalline solid. 1H-NMR (400 MHz, CDCl3) delta: 2.70 (3H, s), 8.18-8.40 (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; dichloromethane; at 20℃; for 17.0h; | Reference Example 33 N-(Methoxycarbonyl)oxy-4-nitrobenzamidine Methyl chlorocarbonate (0.47 ml) was added to methylene chloride (10 ml)-THF (10 ml) solution of <strong>[1613-86-1]N-hydroxy-4-nitrobenzamidine</strong> (1.0 g) and pyridine (0.67 ml) under ice-cooling, and the mixture was stirred at room temperature for 17 hours. The reaction solution was concentrated under reduced pressure, water was added to the resulting residue, and the thus obtained crystals were collected by filtration. The product was washed with diethyl ether and methanol and then dried to obtain the title compound (979 mg) as a crystalline solid. 1H-NMR (400 MHz, DMSO-d6) delta: 3.79 (3H, s), 7.12 (2H, br s), 7.96 (2H, d, J=9.0 Hz), 8.30 (2H, d, J=8.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 85℃; for 2.0h;Inert atmosphere; | Synthesis of N-Hydroxy-4-nitro-benzamidine Hydroxylamine hydrochloride (1.9 g, 27.2 mmol) then sodium carbonate (2.2 g, 20.4 mmol) were added to a stirred solution of 4-nitro-benzonitrile (1 g, 6.8 mmol) in ethanol (20 mL) and water (8 mL). The resulting mixture was refluxed at 85 C. under an atmosphere of nitrogen for 2 hours. The volatiles were then evaporated and the residue was extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and evaporated to afford 1.2 g (98%) of N-hydroxy-4-nitro-benzamidine. 1H NMR: (DMSO-d6): delta 10.2 (s, 1H), 8.24 (d, 2H), 7.97 (d, 2H), 6.03 (s, 2H). |
88% | With ethanol; water; hydroxylamine; at 20℃;Heating / reflux; | Reference Example 25Preparation of 4-(5-Methyl-[ 1 ,2,4]oxadiazol-3 -yl)-phenylamine <n="69"/>Reference Example 25A: iV-Hydroxy-4-nitro-benzamidine.To a stirred solution of 4-nitrobenzonitrile (3.17 g, 21.4 mmol) in absolute ethanol(100 mL) was added hydroxylamine (5 mL of a 50% w/w solution in water, 81 mmol). Mixture heated to reflux for 2.5 hour and then cooled to RT overnight. Ethanol was evaporated under reduced pressure; the residue was mixed with 100 mL water, and stirred for30 minutes. The bright yellow solid was filtered, washed with water (2 x 25 mL), and then dried overnight under high vacuum (3.67 g, 88% yield, -93% pure).1H NMR (300.132 MHz, DMSO-d6) delta 10.12 (s, IH), 8.24 (d, J= 8.4 Hz, 2H), 7.95 (d, J= 8.4 Hz, 2H), 6.04 (s, 2H). |
With hydroxylamine hydrochloride; potassium carbonate; In methanol; for 14.0h;Heating / reflux; | Reference Example 22 N-hydroxy-4-nitrobenzamidine Potassium carbonate (12.44 g) was added to a methanol (300 ml) solution of 4-nitrobenzcyanide (4.44 g) and hydroxylamine hydrochloride (6.25 g), and the mixture was stirred under reflux for 14 hours. After cooling and subsequent removal of the insoluble material by filtration, the filtrate was concentrated under reduced pressure, and water was added to the thus obtained residue. After extraction with ethyl acetate, the organic layer was washed with water and saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the thus obtained residue was washed with diisopropyl ether and n-hexane and then dried to obtain the title compound (4.80 g) as a crystalline solid. 1H-NMR (400 MHz, DMSO-d6) delta: 6.06 (2H, s), 7.94 (2H, d, J=9.0 Hz), 8.22 (2H, d, J=9.0 Hz), 10.13 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With triethylamine; In dichloromethane; at 0 - 20℃; for 4.25h; | Reference Example 25B:(E)-N'-acetoxy-4-nitrobenzimidamide.To a stirred solution ofiV-Hydroxy-4-nitro-benzamidine (600 mg, 3.31 mmol) inDCM (10 mL) cooled to 0 C was added triethylamine (1.2 mL, 8.61 mmol) followed by acetyl chloride (0.30 mL, 4.3 mmol). Mixture was stirred for 1.25 h at 0 C then warmed to room temperature for 3 h. Reaction was diluted with EtOAc (50 mL) and extracted with water (50 mL). Organic extract was dried over MgSO4, filtered, and evaporated under reduced pressure to give a solid which was recrystallized from 95% EtOH (170 mg, 23% yield). MS: m/z 224 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N'-hydroxy-4-nitrobenzimidamide In acetonitrile at 20℃; for 3h; | 5.1. General procedure for the synthesis of N’-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}arylcarboximidamide (4a-g) General procedure: To a solution of indomethacin 1 (1.5 mmole, 0.53 g) in 30 mlacetonitrile, the N,N’-carbonyldiimidazole CDI (11 mmole, 1.2 g) wasadded and the mixture was stirred at room temperature for 30 mins. Therespective amidoximes 3a-g (10 mmole) was then added and stirred forfurther 3 hrs. After completion of reaction (monitored with TLC), theformed precipitate was collected by filtration, washed several times withacetonitrile, dried and used without further purification to give 3a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: 1H-indazole-6-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (Z)-N'-hydroxy-4-nitrobenzimidamide In N,N-dimethyl-formamide at 20℃; for 24h; | 4.1.1. General procedures for the synthesis of amidoximes 6a-v General procedure: To a solution of 1H-indazole-6-carboxylic acid 5 (1 mmol) in DMF (5 mL), EDC (1.3 mmol) and HOAt (1 mmol) were added. The amidoximes 3a-v (1 mmol) were added after 30 min of stirring at room temperature. The resulting mixture was stirred for 24 h at room temperature. The mixture was extracted with EtOAc after adding 30 mL of water, washed three times with water, and once with brine. The mixed organic layer was dried with Na2SO4 and then evaporated at reduced pressure. Finally, using silica gel column chromatography, the resulting compounds 6a-v were purified and isolated as white powders in 50-70% yields. |
50% | Stage #1: 1H-indazole-6-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (Z)-N'-hydroxy-4-nitrobenzimidamide In N,N-dimethyl-formamide at 20℃; for 24h; | 4.1.1. General procedures for the synthesis of amidoximes 6a-v General procedure: To a solution of 1H-indazole-6-carboxylic acid 5 (1 mmol) in DMF (5 mL), EDC (1.3 mmol) and HOAt (1 mmol) were added. The amidoximes 3a-v (1 mmol) were added after 30 min of stirring at room temperature. The resulting mixture was stirred for 24 h at room temperature. The mixture was extracted with EtOAc after adding 30 mL of water, washed three times with water, and once with brine. The mixed organic layer was dried with Na2SO4 and then evaporated at reduced pressure. Finally, using silica gel column chromatography, the resulting compounds 6a-v were purified and isolated as white powders in 50-70% yields. |