Dimethyl Sulfoxide → 1-[3,5-Bis(methylamino)phenyl]-2-(methanesulfonyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 19.2 g. of sodium hydride (50% dispersion in oil) and 56.1 g. of dimethylsulfone in 200 ml. of absolute dimethylsulfoxide was stirred with the exclusion of moisture for 3 hours at 50° C. and then treated at 25° C. with 41.8 g. of methyl 3,5-bis-(N-methylacetamido)benzoate. The mixture was stirred for 18 hours at 25° C., diluted with 2 liters of water, adjusted to pH 7 with glacial acetic acid and extracted with 9 liters of ethyl acetate. The ethyl acetate solution was washed with 3 liters of water, dried over magnesium sulfate and evaporated in vacuo. Recrystallization of the residue from ethanol yielded 3',5'-bis(methylamino)-2-methylsulfonylacetophenone, having a melting point of 144°-146° C.

Provenance & Evidence