Hydrochloric Acid → N-(2-ethylhexyl)benzisothiazolin-3-one

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Reaction Steps

2-chlorosulphenylbenzoyl chloride (10.35 parts; 0.005M) was slowly added to a stirred solution of 2-ethylhexylamine (29.8 parts; 0.23M;) in diethylether (150 ml) at below 5° C. The reactants were then stirred overnight, allowing the temperature to rise to 18° to 20° C. Iced water was then added and the mix made just acid to Congo red by dropwise addition of of concentrated hydrochloric acid, keeping the temperature below 5° C. The ether layer was then separated and dried over magnesium sulphate. The solution was then filtered and the ether evaporated leaving a syrupy oil. This was boiled with petroleum ether (bp 60°-80° C.), the ether layer decanted from some tarry material and then evaporated to dryness leaving a dark yellow oil. This oil was purified by high vacuum distillation in a Kugelrohr and 8.4 parts pale yellow liquid obtained (Yield 64% theory).

Provenance & Evidence