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Names | |
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Preferred IUPAC name
N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide | |
Identifiers | |
3D model (
JSmol)
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ChEMBL | |
ChemSpider | |
MeSH | Sematilide |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
|
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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).
|
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.
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).
![]() | |
Names | |
---|---|
Preferred IUPAC name
N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide | |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
MeSH | Sematilide |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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.
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).