Sematilide

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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

File:Sematilide synthesis.svg
Synthesis of sematilide

Sematilide can be synthesized from benzocaine (1).[1][2] Reaction with mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4-[(methylsulfonyl)amino]benzoate (2). Chlorination with thionyl chloride gives 4-[(methylsulfonyl)amino]benzoyl chloride. Amide formation with N,N-diethylethylenediamine (3) then concludes the synthesis of sematilide (4).

References

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  2. David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, U.S. patent 4544654 (1985 to Schering A.G.)

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