Potassium Cyanide → 4-Aminothiane-4-carbonitrile

Participants

Reaction Steps

To a solution of tetrahydro-4H-thiopyran-4-one (500 mg) in water/ethanol (10 mL/10 mL) was added potassium cyanide (1.4 g) and ammonium chloride (1.15 g) and the mixture was stirred at room temperature for 4 days. To the reaction mixture was added diethylether and an aqueous 1N sodium hydroxide solution and the mixture was stirred. The organic layer was separated and the aqueous layer was extracted with diethylether and ethyl acetate. The combined organic layer was dried over calcium chloride and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=70/30 to 30/70) to give 4-amino-4-cyano-tetrahydro-4H-thiopyrane (315 mg) as a colorless solid.

Provenance & Evidence