Thionyl Chloride → 2-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride

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Reaction Steps

10.0 g (0.042 mol) of 4-(2-furylmethylthio)-2-hydroxymethyl-3-methylpyridine are dissolved in methylene chloride (100 ml), 1.2 equivalents of thionyl chloride are added dropwise at RT and the mixture is stirred at RT for 20 h. It is concentrated completely and the title compound is obtained as an oily residue, which gradually crystallizes and, if desired, can also be used as a solution in ethanol directly for reaction with substituted 2-mercaptobenzimidazoles. For purification, the residue is recrystallized from hot isopropanol with the addition of active charcoal. 9.0 g (74% of theory) of the title compound are obtained as colorless crystals of m.p. 159-161° C. (decomp.).

Provenance & Evidence