Potassium Cyanide → 4-Aminothiane-4-carbonitrile

Participants

Reaction Steps

To a solution of potassium cyanide (5.6 g) and ammonium chloride (5.06 g) in water (17 mL) was added a solution of tetrahydro-4H-thiopyran-4-one (10 g) in methanol (22 mL), and the mixture was refluxed under heating overnight. After cooling to room temperature, to the reaction mixture was added an aqueous 1N sodium hydroxide solution, and the mixture was extracted with diethylether. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and to a solution of the resultant residue in diethylether was added a solution of 4N hydrochloric acid in ethyl acetate. The precipitates were collected by filtration to give 4-amino-tetrahydrothiopyran-4-carbonitrile (13.6 g, yield: 88%) as a colorless solid.

Provenance & Evidence