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【结 构 式】 
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【分子编号】24334 【品名】10-methoxy-5H-dibenzo[b,f]azepine-5-carbonyl chloride 【CA登记号】 |
【 分 子 式 】C16H12ClNO2 【 分 子 量 】285.72952 【元素组成】C 67.26% H 4.23% Cl 12.41% N 4.9% O 11.2% |
合成路线1
该中间体在本合成路线中的序号：(II)Reaction of 10-methoxy-5H-dibenzo[b,f]azepine (I) with phosgene in toluene produced the dibenzoazepine-5-carbonyl chloride (II). This was converted to urea (III) upon treatment with ethanolic ammonia. Acidic hydrolysis of the enol ether function of (III) afforded ketone (IV). Then, reduction of the ketone (IV) to the target alcohol was accomplished either by catalytic hydrogenation over copper chromite or by means of NaBH4 in aqueous EtOH.
| 【1】 Garrett, J.; Soares-da-Silva, P.; Freitas, A.P.; Cunha, R.A.; Benes, J.; Parada, A.; Learmonth, D.A.; Alves, P.C.; Figueiredo, A.; Anticonvulsant and sodium channel-blocking properties of novel 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide derivatives. J Med Chem 1999, 42, 14, 2582. |
| 【2】 Schindler, W. (Novartis AG); Process for the preparation of a new azepine deriv.. DE 2011045; GB 1310120 . |
| 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) | 24333 | 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene | 4698-11-7 | C15H13NO | 详情 | 详情 |
| (II) | 24334 | 10-methoxy-5H-dibenzo[b,f]azepine-5-carbonyl chloride | C16H12ClNO2 | 详情 | 详情 | |
| (III) | 24335 | 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide | C16H14N2O2 | 详情 | 详情 | |
| (IV) | 33774 | 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide | 28721-07-5 | C15H12N2O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)1) The reaction of 10-methoxy-5H-dibenz[b,f]azepine (I) with phosgene in hot toluene gives 10-methoxy-5H-dibenz[b,f]azepine-5-carbonyl chloride (II), which is treated with NH3 in refluxing ethanol to afford 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide (III). Finally, this compound is hydrolyzed with refluxing 2N HCl.
| 【1】 Schindler, W. (Novartis AG); Process for the preparation of new azepine deriv.. DE 2011087 . |
| 【2】 Castaner, J.; Prous, J.; Oxcarbazepine. Drugs Fut 1986, 11, 10, 844. |