HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → ethyl 1-phenyl-5-[(phenylcarbonyl)amino]-1H-pyrazole-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate | HCID 23630921 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | ethyl 1-phenyl-5-[(phenylcarbonyl)amino]-1H-pyrazole-3-carboxylate | HCID 68409669 | 76.2% |
Reaction Steps
To a solution of ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate (498 mg) synthesized according to the method described in WO2004/98589 in N,N-dimethylacetamide (10 mL) were added N-ethyldiisopropylamine (417 mg) and benzoyl chloride (453 mg) at room temperature. After stirring at the same temperature for 18 hr, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=6:1→3:1) to give the title compound as colorless crystals (yield 550 mg, yield 76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08334301B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-c3bcb1c8145d4aada89d385e64ea4173 |
| Source note | uspto-grants-2012_12 |