1,3-Dichloroacetone → 4-Thiazolol, 4-(chloromethyl)-2-[(dimethylamino)methyl]-4,5-dihydro-

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Reaction Steps

To a flask were added 44.5 g. of dimethylaminothioacetamide, hydrochloride, 40.4 g. of 1,3-dichloropropanone, 224 ml. of 1,2-dichloroethane and 53.4 g. of sodium bicarbonate. An endothermic reaction took place and cooled the mixture to 13° on initial mixing. The mixture was then stirred overnight at ambient temperature, and the reaction was found to be essentially complete after 24 hours, by thin layer chromatography. The tlc system is silica gel, eluting with chloroform:methanol:ammonium hydroxide, 36:4:1. The mixture was then filtered, and the filter cake was washed with 1,2-dichloroethane. The filtrate was evaporated to dryness under vacuum to obtain 59.5 g. of crude product, which was washed with ethyl acetate. The washed solids were dried in air, to obtain 52.5 g. of substantially pure product, m.p. 90°-92°.

Provenance & Evidence