Triethylamine → O-isopropylsulfonyl-alpha-chloro-2,6-dichlorobenzaldoxime

Participants

Reaction Steps

A 3.6 (0.036 mol) sample of triethylamine was added slowly to a cooled mixture (ice bath) of 7.8 g (0.035 mol) alpha-chloro-2,6-dichlorobenzaldoxime (U.S. Pat. No. 3,234,255) and 5.5 g (0.035 mol) isopropylsulfonyl chloride in 125 ml diethyl ether. The reaction was slightly exothermic. The reaction mixture was filtered to remove a small amount of salts and the filtrate was evaporated under reduced pressure to give a yellow oil. The oil was chromatographed through a silica gel column with hexane/dichloromethane elution. O-isopropylsulfonyl-alpha-chloro-2,6-dichlorobenzaldoxime (white solid, m.p. 48°-50° C.) was eluted from the column with dichloromethane. Elemental analysis for C11H12Cl3NO3S showed: %S, calc. 9.3, found 8.1; %Cl, calc. 30.9, found 32.8.

Provenance & Evidence