Sematilide

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Sematilide
Names
Preferred IUPAC name
N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Sematilide
UNII
  • InChI=1S/C14H23N3O3S/c1-4-17(5-2)11-10-15-14(18)12-6-8-13(9-7-12)16-21(3,19)20/h6-9,16H,4-5,10-11H2,1-3H3,(H,15,18) checkY
    Key: KHYPYQZQJSBPIX-UHFFFAOYSA-N checkY
  • InChI=1/C14H23N3O3S/c1-4-17(5-2)11-10-15-14(18)12-6-8-13(9-7-12)16-21(3,19)20/h6-9,16H,4-5,10-11H2,1-3H3,(H,15,18)
    Key: KHYPYQZQJSBPIX-UHFFFAOYAU
  • O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C
Properties
C14H23N3O3S
Molar mass 313.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

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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