sematilide
Sign in to saveSematilide 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.
Research
56 papersvia PubMed
Wikidata facts
- Mass
- 313.146
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- chemical formula
- C₁₄H₂₃N₃O₃S
- canonical SMILES
- CCN(CC)CCNC(=O)C1=CC=C(C=C1)NS(=O)(=O)C
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Article
2 sectionsContents
- Synthesis
- References
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== class=skin-invert-image|thumb|center|500px|Synthesis of sematilide Sematilide can be synthesized from benzocaine (1). 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).