Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | HCID 23114614 | HCID 23114614 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 23114853 | HCID 23114853 | 68% |
Reaction Steps
In dichloromethane (6 ml) was dissolved (E)-3-[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]acrylic acid (370 mg, 0.822 mmol). To the resulting solution were added thionyl chloride (2.00 ml) and N,N-dimethylformamide (one drop). The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated to dryness. The residue thus obtained was dissolved in dichloromethane (6 ml), followed by the addition of aqueous concentrated ammonia (2.00 ml). After stirring at room temperature for 2 hours, the reaction mixture was diluted with dichloromethane. The diluted mixture was washed with water, 0.1N hydrochloric acid and brine, dried over magnesium sulfate, and concentrated. The solid thus obtained was recrystallized from ethanol to give the title compound (250 mg, 0.558 mmol, 68%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932271B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-38ab79d32e9348a9b0489b3052c41661 |
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| Source note | uspto-grants-2011_04 |
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