Ammonia → 4-Aminothiane-4-carbonitrile

Participants

Reaction Steps

To a solution of tetrahydro-4H-thiopyran-4-one (215 g, 1.85 mol) in ethanol (1500 mL) was bubbled ammonia gas at 0° C. After 4 hours, trimethylsilanecarbonitrile (184 g, 1.86 mol) was added dropwise and then the reaction mixture was allowed to warm to ambient temperature. After 5 hours, the reaction mixture was concentrated under reduced pressure and then diluted with hexane (800 mL). The mixture was filtered, and the solids were washed with hexanes (2×400 mL) and dried under reduced pressure to afford 4-aminotetrahydro-2H-thiopyran-4-carbonitrile. The material was used without further purification.

Provenance & Evidence