3-Chlorobenzamide → 5-(3-chlorophenyl)-2H-1,3,4-oxathiazol-2-one

Participants

Reaction Steps

m-Chlorobenzamide (75 g, 0.48 mol) and chlorocarbonylsulfenyl chloride (79 g, 0.6 mol, 25% excess) were reacted as described in Example 2 for 1.5 hours. Volatile components were removed under reduced pressure. The dark brown oil was taken up in hot cyclohexane, and the mixture was filtered. Cooling resulted in separation of a dark orange solid. The solid, recrystallized twice from hot ethyl acetate, gave 64.21 g (0.316 mol, 65.8%) of off-white solid, m.p. 83°-84.5°.

Provenance & Evidence