Ammonia → 3-Fluoro-4-methylbenzenesulfonamide
Reaction equation
[NH3:1].[F:2][C:3]1[CH:4]=[C:5]([S:10](Cl)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[CH3:9]>>[F:2][C:3]1[CH:4]=[C:5]([S:10]([NH2:1])(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[CH3:9]Participants
3
Procedure
To ˜20 mL of liquid ammonia at −78° C. was added 2.1 g (10 mmol) of 3-fluoro-4-methyl benzenesulfonyl chloride. The excess ammonia was then naturally evaporated to dryness overnight at room temperature. The crude sulfonamide was partitioned methylene chloride (100 mL) and water (100 mL). The aqueous phase was further extracted with methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate. Evaporation of the solvents afforded 1.9 g of 3-fluoro-4-methylbenzenesulfonamide as a solid.
Workup
- customThe excess ammonia was then naturally evaporated to dryness overnight at room temperature
- customThe crude sulfonamide was partitioned methylene chloride (100 mL) and water (100 mL)
- extractionThe aqueous phase was further extracted with methylene chloride
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- customEvaporation of the solvents
Sources & evidence
- ORD record
- ord-b6eb31ab78bd44929e99e26a1573795f
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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