Sematilide

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title: "Sematilide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["sulfonamides", "antiarrhythmic-agents", "benzamides", "diethylamino-compounds", "mesyl-compounds"] topic_path: "general/sulfonamides" source: "https://en.wikipedia.org/wiki/Sematilide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | verifiedrevid = 464389005 | ImageFile=Sematilide.png | ImageClass = skin-invert-image | ImageSize=200px | PIN=N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide | OtherNames= |Section1={{Chembox Identifiers | UNII_Ref = | UNII = 0NHB13IN3R | UNII1_Ref = | UNII1 = 1B8MC21ZI2 | UNII1_Comment = (HCl) | ChemSpiderID_Ref = | ChemSpiderID = 52715 | 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) | InChIKey = KHYPYQZQJSBPIX-UHFFFAOYAU | ChEMBL_Ref = | ChEMBL = 95804 | StdInChI_Ref = | StdInChI = 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) | StdInChIKey_Ref = | StdInChIKey = KHYPYQZQJSBPIX-UHFFFAOYSA-N | CASNo_Ref = | CASNo=101526-83-4 | CASNo1_Ref = | CASNo1 = 101526-62-9 | CASNo1_Comment =(HCl)

| PubChem=58505 | SMILES = O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C | MeSHName=Sematilide |Section2={{Chembox Properties | Formula=C14H23N3O3S | MolarMass=313.42 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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

::figure[src="https://upload.wikimedia.org/wikipedia/commons/b/bc/Sematilide_synthesis.svg" caption="Synthesis of sematilide"] ::

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

References

  1. (1987). "Rational design of 4-[(methylsulfonyl)amino]benzamides as class III antiarrhythmic agents". Journal of Medicinal Chemistry.
  2. David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, {{US patent. 4544654 (1985 to Schering A.G.)

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sulfonamidesantiarrhythmic-agentsbenzamidesdiethylamino-compoundsmesyl-compounds