Aniline → N-phenyl-3-chloropropylsulfonamide

Participants

Reaction Steps

3-Chloropropylsulfonyl chloride 1 (1.456 g, 8.23 mmol) was dropwise added to a solution of aniline (0.5 ml, 8.23 mmol) in pyridine (5 ml) with cooling at −20° C. 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. From the intermediate 3j, the desired compound 4j (yield: 57%) was yielded as a pale yellow solid in a manner as described in Preparation 1. IR (CHCl3)cm−1: 3020, 1598, 1495, 1315, 1139. NMR (CDCl3) δ: 2.46-2.60 (2H, m, CH2), 3.34-3.42 (2H, m, CH2), 3.78 (2H, t, J=6.6 Hz, CH2), 7.10-7.40 (5H, m, C6H5).

Provenance & Evidence