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【结 构 式】 
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【分子编号】34283 【品名】7-chloro-N-(3,4-dichlorophenyl)-1,1-dioxo-5-(1-pyrrolidinyl)-2,3-dihydro-1H-2H-benzothiepine-4-carboxamide 【CA登记号】 |
【 分 子 式 】C21H19Cl3N2O3S 【 分 子 量 】485.81764 【元素组成】C 51.92% H 3.94% Cl 21.89% N 5.77% O 9.88% S 6.6% |
合成路线1
该中间体在本合成路线中的序号：(VI)The oxidation of 7-chloro-5-hydroxy-2,3-dihydro-1-benzothiepin (I) with H2O2 in acetic acid - water gives 7-chloro-5-hydroxy-2,3-dihydro-1-benzothiepin-1,1-dioxide (II), which by reaction with pyrrolidine (III) and p-toluenesulfonic acid in refluxing benzene is converted into 7-chloro-5-pyrrolidino-2,3-dihydro-1-benzothiepin-1,1-dioxide (IV). The condensation of (IV) with 3,4-dichlorophenyl isocyanate (V) in hot THF yields N-(3,4-dichlorophenyl)-7-chloro-5-pyrrolidino-2,3-dihydro-1-benzothiepin-4-carboxamide-1,1-dioxide (VI), which is finally hydrolyzed with HCl in refluxing ethanol - water.
| 【1】 Rosen, M.H.; 1-Benzothiepin-4-carboxamides. BE 0833787; CA 1066279; CH 617433; DE 2542329; FR 2285872; US 4185109 . |
| 【2】 Serradell, M.N.; Castaner, J.; Enolicam sodium. Drugs Fut 1984, 9, 7, 508. |
| 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) | 34279 | 7-chloro-2,3-dihydro-1-benzothiepin-5-ol | C10H9ClOS | 详情 | 详情 | |
| (II) | 34280 | 7-chloro-5-hydroxy-2,3-dihydro-1H-2H-benzothiepine-1,1-dione | C10H9ClO3S | 详情 | 详情 | |
| (III) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
| (IV) | 34281 | 7-chloro-5-(1-pyrrolidinyl)-2,3-dihydro-1H-2H-benzothiepine-1,1-dione | C14H16ClNO2S | 详情 | 详情 | |
| (V) | 34282 | 1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate | 102-36-3 | C7H3Cl2NO | 详情 | 详情 |
| (VI) | 34283 | 7-chloro-N-(3,4-dichlorophenyl)-1,1-dioxo-5-(1-pyrrolidinyl)-2,3-dihydro-1H-2H-benzothiepine-4-carboxamide | C21H19Cl3N2O3S | 详情 | 详情 |