Aniline → N-phenyl-3-chloropropylsulfonamide

Participants

Reaction Steps

3-Chloropropylsulfonyl chloride 1 (1.456 g,8.23 mmol) was added dropwise to a solution of aniline (0.5 ml, 8.23 mmol) in pyridine (5 ml) with cooling at -20° to -30° C. over about 5 minutes. After the completion of the addition, the reaction mixture was stirred for another 45 minutes at room temperature. The reaction mixture was concentrated in vacuo and the residue was subjected to column chromatography on silica gel. From the fraction eluted with a mixture of ethyl acetate/n-hexane (1:2), 1.683 g (88%) of N-phenyl-3-chloropropylsulfonamide (intermediate 3j) was obtained as a yellow oil, which, when treated in a manner similar to that described in Preparation 1, gave the objective compound 4j as a pale yellow solid (yield 57%).

Provenance & Evidence