Sematilide


Sematilide is an antiarrhythmic agent. It is the same structure as for procainamide, differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen.

Synthesis

Sematilide can be synthesized from benzocaine. Reaction with mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4-benzoate. Chlorination with thionyl chloride gives 4-benzoyl chloride. Amide formation with N,''N''-diethylethylenediamine then concludes the synthesis of sematilide.