| Revision as of 13:57, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456575231 of page Sematilide for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 14:59, 30 October 2023 edit 2.102.126.68 (talk)No edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 464389005 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| ImageFile=Sematilide.png |
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| UNII = 0NHB13IN3R |
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| ImageSize=200px |
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| verifiedrevid = 418111793 |
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| PIN=''N''--4-(methanesulfonamido)benzamide |
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|ImageFile=Sematilide.png |
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| OtherNames= |
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|ImageSize=200px |
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|IUPACName=''N''-(2-Diethylaminoethyl)-4-methanesulfonamidobenzamide |
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|OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0NHB13IN3R |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 1B8MC21ZI2 |
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| UNII1_Comment = (]) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 52715 |
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| ChemSpiderID = 52715 |
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| 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) |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KHYPYQZQJSBPIX-UHFFFAOYSA-N |
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| StdInChIKey = KHYPYQZQJSBPIX-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 101526-62-9 --> |
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| CASNo=101526-83-4 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| PubChem=58505 |
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| CASNo1 = 101526-62-9 |
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| SMILES = O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C |
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| CASNo1_Comment =(]) |
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| MeSHName=Sematilide |
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| PubChem=58505 |
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| SMILES = O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C |
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| MeSHName=Sematilide |
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|Section2={{Chembox Properties |
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| Formula=C<sub>14</sub>H<sub>23</sub>N<sub>3</sub>O<sub>3</sub>S |
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| Formula=C<sub>14</sub>H<sub>23</sub>N<sub>3</sub>O<sub>3</sub>S |
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| MolarMass=313.42 g/mol |
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| MolarMass=313.42 g/mol |
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|Section3={{Chembox Hazards |
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'''Sematilide''' is an ]. It is the same structure as for ], differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen. |
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==Synthesis== |
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benzamides as class III antiarrhythmic agents". Journal of Medicinal Chemistry 30 (5): 755–758. doi:10.1021/jm00388a001.</ref> Patent:<ref>David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, {{US patent|4544654}} (1985 to Schering A.G.).</ref>]] |
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The reaction between Benzocaine (Ethyl 4-Aminobenzoate) ('''1''') and mesyl chloride gives the sulfonamide, Ethyl 4-(Methylsulfonamido)benzoate . Base saponification followed by the removal of the water from the reaction mixture gives 4-benzoic acid sodium salt ('''2'''). Halogenation with thionyl chloride gives 4-Benzoyl Chloride . Amide formation with N,N-Diethylethylenediamine ('''3''') then concludes the synthesis of ''Sematilide'' ('''4'''). |
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==References== |
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{{Reflist}} |
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] |
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] |
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] |
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] |
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{{organic-compound-stub}} |