Water → 5-Chloro-2-[(3-chloropropyl)thio]pyridine

Temperature

60 °C

5-Chloropyridine-2-thiol (600 mg, 4.12 mmol) synthesized in Example (119a) was dissolved in methanol (15 mL), and 28% sodium methoxide/methanol solution (0.95 mL, 4.94 mmol) and 1-bromo-3-chloropropane (0.61 mL, 6.18 mmol) were added, followed by stirring at 60° C. for 1.5 hours. The reaction solution was cooled to room temperature, water (40 mL) was added, and extraction was carried out twice with ethyl acetate (40 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and vacuum drying was carried out to afford the desired compound (849 mg, yield 92%) as a colorless oil.

1. temperatureThe reaction solution was cooled to room temperature
2. extractionextraction
3. washThe organic layer was washed with saturated brine
4. dry with materialsubsequently dried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure, and vacuum
6. customdrying

ORD record

ord-f8f02c09ac174a1099a77712417b481c

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2