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

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).

References