1,3-Dichloroacetone → 1-(4-(chloromethyl)thiazol-2-yl)-N,N-dimethylmethanamine hydrochloride

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Reaction Steps

To a flask were added 150 ml. of 1,2-dichloroethane, 38.5 g. of dimethylaminothioacetamide, hydrochloride, 34.9 g. of 1,3-dichloropropanone and 46.2 g. of sodium bicarbonate. The mixture was stirred at ambient temperature for 22 hours, and the mixture was filtered. The filter cake was washed with 50 ml. of 1,2-dichloroethane, and the combined filtrate was added dropwise to a solution of 20 ml. of thionyl chloride in 100 ml. of 1,2-dichloroethane. The temperature of the mixture was held at 20°-25° during the addition, and the mixture was stirred at ambient temperature overnight after the addition was complete. It was then heated to 65°-70° and held at that temperature for 30 minutes. To the reaction mixture was then added 75 ml. of water, and the mixture was stirred for 30 minutes before the layers were allowed to separate. The organic layer was then extracted with 38 ml. of deionized water, and then with 18 ml. of deionized water. All of the aqueous layers were combined, and examined by tlc, using the system described above, which showed that the aqueous phase contained the desired product.

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