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【结 构 式】 
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【分子编号】29005 【品名】2-acetyl-N-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide 【CA登记号】 |
【 分 子 式 】C17H17ClN2O3S 【 分 子 量 】364.85236 【元素组成】C 55.96% H 4.7% Cl 9.72% N 7.68% O 13.16% S 8.79% |
合成路线1
该中间体在本合成路线中的序号：(V)The acetylation of 1,2,3,4-tetrahydroisoquinoline (I) with acetic anhydride gives 2-acetyl-1,2,3,4-tetrahydroisoquinoline (II), which is sulfonated with chloro sulfonic acid in methylene chloride yielding 2-acetyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline (III). The reaction of (III) with 3-chloroaniline (IV) and triethylamine in refluxing acetone affords 2-acetyl-7-(3-chlorophenylamino sulfonyl)-1,2,3,4-tetrahydroisoquinoline (V), which is deacetylated by a treatment with HCl in refluxing butanol to 7-(3-chlorophenylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline (VI). Finally, this compound is condensed with bis(chlorosulfonyl)imide (VII) [prepared with chlorosulfonic acid (VIII) and chlorosulfonyl isocyanate (IX)] in acetonitrile containing triethylamine.
| 【1】 Ali Fadia E. (SmithKline Beecham Corp.); N,N'-Bis[substituted-1,2,3,4-tetrahydroisoquinolino]disulfonylimides and antiallergic compositions and method of use. DD 158240; EP 0038177; US 4135935 . |
| 【2】 Serradell, M.N.; Chu, S.S.; Castaner, J.; SKF-88046. Drugs Fut 1985, 10, 1, 42. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 14124 | 1,2,3,4-Tetrahydroisoquinoline | 91-21-4 | C9H11N | 详情 | 详情 |
| (II) | 29003 | 1-[3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone | C11H13NO | 详情 | 详情 | |
| (III) | 29004 | 2-acetyl-1,2,3,4-tetrahydro-7-isoquinolinesulfonyl chloride | C11H12ClNO3S | 详情 | 详情 | |
| (IV) | 25239 | 3-chloroaniline; 3-chlorophenylamine | 108-42-9 | C6H6ClN | 详情 | 详情 |
| (V) | 29005 | 2-acetyl-N-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide | C17H17ClN2O3S | 详情 | 详情 | |
| (VI) | 29006 | N-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide | C15H15ClN2O2S | 详情 | 详情 | |
| (VII) | 29007 | Bis(chlorosulfonyl)imide | HCl2NO4S2 | 详情 | 详情 | |
| (VIII) | 29008 | Chlorosulfonic acid | 7790-94-5 | HClO3S | 详情 | 详情 |
| (IX) | 14101 | Chlorosulfonyl isocyanate | 1189-71-5 | CClNO3S | 详情 | 详情 |