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CAS No. : | 1772-01-6 | MDL No. : | MFCD00085159 |
Formula : | C6H7N3O | Boiling Point : | No data available |
Linear Structure Formula : | NC5H4C(NH2)NOH | InChI Key : | - |
M.W : | 137.14 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
1.63 g (60%) | With triethylamine; In N-methyl-acetamide; dichloromethane; N,N-dimethyl-formamide; | 5-(3-Chloro-5-methoxy-pyrid-4-yl)-3-(2-pyridyl)-1,2,4-oxadiazole A mixture of <strong>[15855-06-8]2-chloro-6-methoxyisonicotinic acid</strong> (1.87 g, 10 mmol) in dichloromethane (15 mL) was treated with 2M oxalyl chloride (15 ml, 30 mmol, dichloromethane) and 3 drops of N,N-dimethylformamide. The mixture was stirred 2 hours at room temperature. The solvent and excess reagent were removed in vacuo. The residue was treated with 2-pyridylamidoxime (1.37 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in dichloromethane (15 mL). The mixture was then heated in dimethylformamide (10 mL) for 1 hours at 120 C. Standard work up, afforded 1.63 g (60%) of 3-(2-pyridyl)-5-(3-chloro-5-methoxy-pyrid-4-yl)-1,2,4-oxadiazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; | 3-(2-Pyridyl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole 3-Fluoro-5-trifluoromethylbenzoyl chloride (0.11 mL, 0.73 mmol) was added in a dropwise manner to a solution of pyridylamidoxime (99.3 mg, 0.73 mmol) in dichloromethane (10 mL) under argon. The reaction mixture was stirred at room temperature for 10 minutes and the solvent was removed in vacuo. DMF (4 ml) was added to the oily residue and the resulting solution was stirred at 120 C. for 16 h under argon. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo. Flash chromatography on silica gel (15%-20% ethyl acetate in hexanes) yielded 150 mg (66.9%, GC/MS product RT 7.59 min, 98% purity) of 3-(2-pyridyl)-5-(3-cyano-5-trifluoromethylphenyl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.86 (d, 1H), 8.40 (s, 1H), 8.24 (d, 1H), 8.18 (d, 1H), 7.90 (dt, 1H), 7.59 (d, 1H), 7.49 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In neat (no solvent); at 80℃; for 0.0833333h;Green chemistry; | A mixture of compound 3b (1.47 mmol), <strong>[22651-87-2]cyclohexanecarboxylic acid anhydride</strong> (1.77 mmol) and HClO4-SiO2 (5 mol %) was stirred at 80 C for 5 min. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature, diluted with dichloromethane (5 mL) and the catalyst was allowed to settle down. Then the reaction mixture was filtered, washed with dichloromethane (5 mL), and the combined organic layers were washed with saturated aq. NaHCO3 and water. The obtained organic layer was dried over anhy. Na2SO4 and concentrated under reduced pressure to get crude compound. The crude was then purified by column chromatography on silica gel using hexane/EtOAc (7:3) as eluents to get pure compound 5j. |