Water → 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide
Reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].C(N(CC)CC)C.O>O1CCOCC1>[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8]Participants
6
Procedure
To a stirred solution of 2,2,2-trifluoroethylamine (1.17 ml, 15 mmol) in dioxane (37 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (3.0 g, 14 mmol) and triethylamine (2.06 ml, 15 mmol). The light yellow suspension was stirred at room temperature for 4 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) to yield 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide (3.18 g, 83%) as a light yellow solid. MS (ISP) 283.9 [(M−H)−].
Workup
- extractionextracted with dichloromethane (3×75 ml)
- washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
- dry with materialdried (MgSO4)
- customevaporated
- customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1)
Sources & evidence
- ORD record
- ord-fababdeaa52c4851a3df810a4461d813
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378417B2
Reaction notes
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