Potassium Cyanide → 4-Aminothiane-4-carbonitrile

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.

1. temperaturethe mixture was refluxed
2. temperatureunder heating overnight
3. extractionthe mixture was extracted with diethylether
4. dry with materialThe organic layer was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. additionto a solution of the resultant residue in diethylether was added a solution of 4N hydrochloric acid in ethyl acetate
8. filtrationThe precipitates were collected by filtration

ORD record

ord-8d7f56609bc84c3bb8f4d21d6f06b8ac

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163759B2