Sematilide

Sematilide

Names
Preferred IUPAC name N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide
Identifiers
CAS Number	101526-83-4 Y 101526-62-9 (HCl) Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL95804 Y
ChemSpider	52715 Y
MeSH	Sematilide
PubChem CID	58505
UNII	0NHB13IN3R Y 1B8MC21ZI2 (HCl) Y
CompTox Dashboard (EPA)	DTXSID0058720
InChI 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) Y Key: KHYPYQZQJSBPIX-UHFFFAOYSA-N Y 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
SMILES O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C
Properties
Chemical formula	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). N verify (what is YN ?) Infobox 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

Synthesis: Patent:

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).