Succinimide → 4-Chloro-2-(1,1,3,3-tetramethylbutyl)-3(2H)-isothiazolone

Participants

Reaction Steps

To a solution of 10.7 g. (0.05 mole) of 2-t-octyl-3-isothiazolone in 100 ml. of chloroform is added in a single portion 13.3 g. (0.1 mole) of N-chlorosuccinimide. The mixture warms somewhat but does not require cooling. After stirring for 2.5 hours, the mixture is filtered giving 7.5 g. of crude succinimide. The filtrate is evaporated under reduced pressure and the residue dissolved in ether. The ether solution is extracted with water, dried over anhydrous magnesium sulfate, and evaporated to a mixture of solid and oil. The oil is washed from the solid with hexane leaving 1.7 g. (14%) of white 4-chloro-2-t-octyl-3-isothiazolone, m.p. 137°-140°.

Provenance & Evidence