Hydrochloric Acid → Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-thiobenzimidate Dihydrochloride

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A mixture of α-[N,N-di(n-hexadecyl)amino]-m-toluonitrile (23.2 g., 0.04 mole), ethanthiol (6.0 ml., 0.08 mole) and chloroform (100 ml.) was saturated with dry hydrogen chloride for 30 minutes at 20°-25° C. It was then stoppered and held for six days at 5° C. The mixture was evaporated in vacuo to a foam which was crystallized by trituration with 1,2-dimethoxyethane. The crude product was recrystallized from hot 1,2-dimethoxyethane/chloroform [24.9 g., 88% yield, Rf 0.79 (4:1, benzene:ethanol on silicic acid), m.p. 109°-111° C⟧

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