Isoamyl mercaptan → 2-Cyano-6-isopentylthiopyridine

Isopentyl mercaptan (0.83 g, 7.9 mmol) was dissolved in tetrahydrofuran (100 ml) and added dropwise to sodium hydride (60% oil, 0.35 g, 8.7 mmol). The reaction mixture was stirred at room temperature for 1 hr. A solution of 2-chloro-6-cyanopyridine (1.00 g, 7.2 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give the titled compound (1.48 g, ca. 100%) as an oil.

1. stirringthe mixture was stirred at room temperature for 18 hrs
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additiondiluted with water
4. extractionextracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. customdried
7. customThe solvent was evaporated under reduced pressure

ORD record

ord-019720b020094960af8d57165c8926ac

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399759B2