Ammonia → HCID 19912246, compound

Participants

Reaction Steps

To a solution of 8.0 g of 3-chloro-2-phenylmethylthio-(1-fluoroethyl)benzene in a mixture of 45 mL of propionic acid and 1.5 mL of water at -10° was added 5.2 mL of liquified chlorine. The reaction was stirred an additional 30 min and then poured into a mixture of ice/water. The aqueous phase was extracted with n-butyl chloride and the combined organic phase was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated to provide an oil. The crude sulfonyl chloride was dissolved in 100 mL of THF, cooled to -78° and treated with 1.6 mL of liquified anhydrous ammonia. The reaction was allowed to slowly warm to room temperature and stirred overnight. The solids were removed by filtration and then concentration provided the crude sulfonamide. Recrystallization from ethanol/water yielded 2.7 g of the title compound as a white solid, mp 151°-153°.

Provenance & Evidence