Pyridine → 4-Methyl-N-(1,2,2,2-tetrachloroethyl)benzamide

Participants

Reaction Steps

A stirred solution of Example 37C (20.0 g, 70.8 mmol) in CH2Cl2(300 mL) at 0° C. was treated with pyridine (10 mL). The reaction mixture was treated dropwise with thionyl chloride (10.4 mL, 141 mmol), and the reaction flask was equipped with a calcium chloride drying tube. The reaction mixture was warmed to ambient temperature and stirred for 4 hours. Concentration of the reaction mixture to a reduced volume and addition of diethyl ether (100 mL) resulted in a precipitate which was filtered off, and the filtrate was concentrated and dried under reduced pressure to provide 19.0 g of the desired product as a white solid.

Provenance & Evidence