Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzenesulfonyl chloride | HCID 7369 | — |
| Reactant | Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate | HCID 23630921 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 68409423 | HCID 68409423 | 69% |
Reaction Steps
Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate (498 mg) synthesized according to the method described in WO2004/98589 and 4-dimethylaminopyridine (21 mg) were dissolved in pyridine (10 mL), and benzenesulfonyl chloride (461 mg) was added at room temperature. After stirring at 85° C. for 8 hr, 1 mol/L hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water and 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=1:1→ethyl acetate), and the obtained solid was washed with a mixed solvent of diisopropyl ether and ethyl acetate to give the title compound as a brown powder (yield 445 mg, yield 69%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08334301B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-f0bae3ff05e64d3c88d8eb78ee7db8cf |
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| Source note | uspto-grants-2012_12 |
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