Thionyl Chloride → HCID 21913840, compound

Participants

Reaction Steps

Thionyl chloride (3.14 mL, 43 mmol) was added over a period of 5 minutes to a chilled (0° C.) solution of 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butan-1-ol (12.95 g, 39.08 mmol) in dichloromethane (130 mL). The reaction was allowed to warm to ambient temperature and was stirred overnight under a nitrogen atmosphere. The reaction mixture was diluted with dichloromethane (130 mL), washed sequentially with saturated aqueous sodium bicarbonate (2×65 mL), water (80 mL) and brine (100 mL), dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide 12.57 g of N-(4-chlorobutyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine as a yellow solid.

Provenance & Evidence