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-4a9a6dca79fb47ae92c4b2616eeeca85

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767665B2