2-Bromopropane → HCID 13645636, compound

Participants

Reaction Steps

N-(3-Chloropropyl)-N-isopropyl-3,4-dichlorobenzenesulfonamide, prepared by reacting 3,4-dichlorobenzenesulfonyl chloride with 3-hydroxypropylamine followed by N-alkylation with 2-bromopropane and displacement of the hydroxyl group by chlorine, (13.94 g), N--CH3 homoveratrylamine (8.23 g), K2CO3 (2.90 g) and Cs2CO3 (7.39 g) in xylene (300 mL) was heated and stirred for 5 days. The reaction was cooled, filtered and stripped to provide a partially solid crude product which was stirred with diethyl ether, filtered and the filtrate stripped to provide 17.11 g. This material was chromatographed on dry-column silica gel (500 g) using ethyl acetate to provide the product which was recrystallized from diethyl ether-hexane to give the impure product (3.95 g) (m.p. 62°-64° C.). A second recrystallization from diethyl ether-hexane provided pure product (3.57 g, m.p. 65°-66° C.).

Provenance & Evidence