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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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

Synthesis:[1] Patent:[2]

The reaction between Benzocaine (Ethyl 4-Aminobenzoate) [94-09-7] (1) and mesyl chloride [124-63-0] gives the sulfonamide, Ethyl 4-(Methylsulfonamido)benzoate [7151-77-1]. Base saponification followed by the removal of the water from the reaction mixture gives 4-[(Methylsulfonyl)amino]benzoic acid sodium salt (2). Halogenation with thionyl chloride gives 4-[(Methylsulfonyl)Amino]Benzoyl Chloride [63421-72-7]. Amide formation with N,N-Diethylethylenediamine [100-36-7] (3) then concludes the synthesis of Sematilide (4).

References

  1. ^ Lumma, William C.; Wohl, Ronald A.; Davey, David D.; Argentieri, Thomas M.; DeVita, Robert J.; Gomez, Robert P.; Jain, Vijay K.; Marisca, Anthony J.; Morgan, Thomas K. (1987). "Rational design of 4-[(methylsulfonyl)amino]benzamides as class III antiarrhythmic agents". Journal of Medicinal Chemistry 30 (5): 755–758. doi:10.1021/jm00388a001.
  2. ^ David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, U.S. patent 4,544,654 (1985 to Schering A.G.).
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