2,6-Lutidine → O-(3-chloropropyl)-alpha-chloro-2,6-dichlorobenzaldoxime

Participants

Reaction Conditions

Reaction Steps

A 3.6 g (0.034 mol) sample of 2,6-dimethylpyridine was added dropwise to a cooled solution (ice bath) of 7.4 g (0.033 mol) alpha-chloro-2,6-dichlorobenzaldoxime and 5.9 g (0.03 mol) 3-chloropropylsulfonyl chloride in 75 ml benzene. The reaction mixture was allowed to warm to 25° C., stirred for 2 hours (a red solid formed) and allowed to stand overnight. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed through a silica gel column with dichloromethane. A semi-crystalline yellow product was eluted from the column. The product was recrystallized from ether/hexane to give 4.3 g of O-(3-chloropropyl)-alpha-chloro-2,6-dichlorobenzaldoxime as a white solid, m.p. 69°-71° C. Elemental analysis for C10H9Cl4NO3S showed: %S, calc. 8.8, found 9.2; %Cl, calc. 38.8, found 37.9.

Provenance & Evidence