Hydrochloric Acid → HCID 178510225, compound

Temperature

0 °C

A solution of 2-(1H-1,2,4-triazol-3-ylthio)ethanol obtained in Reference Example 16 (7.34 g, 50.6 mmol) in DMF (50 mL) was added to a solution of 60% sodium hydride (oil dispersion, 4.91 g, 123 mmol) in DMF (50 mL) at 0° C. The mixture was stirred at 0° C. for 15 min, and then at room temperature for 30 min. A solution of 2-chloropyridine-4-carbonitrile (6.80 g, 49.1 mmol) in DMF (50 mL) was added at 0° C., and the mixture was stirred at 0° C. for 15 min, and then at room temperature for 2 hr. The mixture was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give the title compound as a white powder (4.01 g, 33%).

1. waitat room temperature for 30 min
2. stirringthe mixture was stirred at 0° C. for 15 min
3. waitat room temperature for 2 hr
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane)

ORD record

ord-f596c0f387e340438931bc7f245195f2

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915267B2