Sodium Cyanide → 5-(2-Cyano-1,1-dimethylethyl)-2-methylamino-1,3,4-thiadiazole

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Reaction Steps

A 20.5 g. portion of the intermediate prepared in Example 1 and 10 g. of NaCN were added to 50 ml. of dimethylsulfoxide and heated at 110°C. for 2 hours. The reaction mixture was then cooled and poured into 300 ml. of water, which was then extracted with a total of 1 liter of ethyl ether. The combined ether extracts were dried over anhydrous Na2SO4, filtered, and evaporated to dryness yielding a dark oil. The oil was chromatographed on a silica gel column, eluting with ethyl acetate. The desired intermediate product, 5-(2-cyano-1,1-dimethylethyl)-2-methylamino-1,3,4-thiadiazole, m.p. 65°-67°C., was isolated in the amount of 750 mg.

Provenance & Evidence