4-(Trifluoromethyl)benzenesulfonyl chloride → N-[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide
Reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH3:15])=[CH:10][CH:9]=1.[F:17][C:18]([F:30])([F:29])[C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O1CCOCC1>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]([CH3:15])[S:25]([C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:29])[F:30])=[CH:24][CH:23]=2)(=[O:27])=[O:26])=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 173 mg (0.8 mmol) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-amine in 2 ml dioxane was treated with 0.15 ml (0.88 mmol) Huinigsbase and 247 mg (1 mmol) 4-(trifluoromethyl)benzenesulfonyl chloride. The reaction mixture was stirred over night at room temperature and extracted with aqueous 10% KHSO4/EtOAc (3×). The aqueous phase was treated with NaHCO3 (pH 7-8) and extracted with CH2Cl2 (3×). The organic phase was dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (9:1) yielded 223 mg (65%) of N-[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 425 (MH+).
Workup
- extractionextracted with aqueous 10% KHSO4/EtOAc (3×)
- additionThe aqueous phase was treated with NaHCO3 (pH 7-8)
- extractionextracted with CH2Cl2 (3×)
- dry with materialThe organic phase was dried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-de9054f607274c53a63db94a3fd23133
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06683201B2
Reaction notes
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