Methanesulfonyl chloride → Flosulide

Participants

Reaction Steps

12.8 g of 5-amino-6-(2,4-difluorophenoxy)-1-indanone in 95 ml of pyridine was combined at 0° C. with 8.3 ml of methanesulfonyl chloride. After 3 hours at 0° C. and 16 hours at 20° C., the mixture was concentrated, the residue taken up in chloroform, the solution washed with 1 N hydrochloric acid, and concentrated. Chromatography of the residue over silica gel with dichloromethane-ethyl acetate yielded 1.2 g of 6-(2,4-difluorophenoxy)-5-bis(methylsulfonyl)amino-1-indanone, mp 190° C. (from toluene) and subsequently 8.9 g of 6-(2,4-difluorophenoxy)-5-methylsulfonylamino-1-indanone, mp 153° C. (from ethanol).

Provenance & Evidence