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【结 构 式】 
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【分子编号】52658 【品名】2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid 【CA登记号】 |
【 分 子 式 】C16H15NO4 【 分 子 量 】285.29944 【元素组成】C 67.36% H 5.3% N 4.91% O 22.43% |
合成路线1
该中间体在本合成路线中的序号：(IV)A new process for the preparation of oxcarbamazepine has been reported: Reaction of 1-phenyl-2,3-dihydro-1H-indol-2-one (I) with NaOH in refluxing THF gives 2-[2-(phenylamino)phenyl]acetic acid (II), which is condensed with dimethyl carbonate (III) by means of butyl lithium in the same solvent to yield 2-[2-[N-(methoxycarbonyl)-N-phenylamino]phenyl]acetic acid (IV). Cyclization of compound (IV) by means of polyphosphoric acid (PPA) at 100 C, followed by treatment of the reaction mixture with hot methanol (65 C) affords 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxylic acid methyl ester (V), which is treated with NaOH in polyethyleneglycol at 100 C to provide 10-methoxy-5H-dibenzo[b,f]azepine (VI). Reaction of (VI) with sodium cyanate in acetic acid gives 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide (VII), which is finally treated with H2SO4.
| 【1】 Kaufmann, D.; Lohse, O.; Zaugg, W.; Funfschilling, P.; Beutler, U. (Novartis AG; Novartis-Erfindungen VmbH); Dibenzo [b,f]azepine derivs. and their preparation. WO 0156992 . |
| 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) | 52656 | 1-phenyl-1,3-dihydro-2H-indol-2-one | C14H11NO | 详情 | 详情 | |
| (II) | 52657 | 2-[2-(phenylamino)phenyl]acetic acid | C14H13NO2 | 详情 | 详情 | |
| (III) | 34197 | dimethyl carbonate | 616-38-6 | C3H6O3 | 详情 | 详情 |
| (IV) | 52658 | 2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid | C16H15NO4 | 详情 | 详情 | |
| (V) | 52659 | methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate | C17H15NO3 | 详情 | 详情 | |
| (VI) | 24333 | 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene | 4698-11-7 | C15H13NO | 详情 | 详情 |
| (VII) | 24335 | 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide | C16H14N2O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)
| 【1】 Kaufmann D, Fuenfschilling PC,Beutler U, et al.2004.A new synthesis of oxcarbazepine using a friedelcrafts cyclization strategy. Tetrahedron Lett,45:5275-5278. |
| 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) | 52658 | 2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid | C16H15NO4 | 详情 | 详情 | |
| (II) | 69515 | methyl 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxylate | C16H13NO3 | 详情 | 详情 | |
| (III) | 52659 | methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate | C17H15NO3 | 详情 | 详情 | |
| (IV) | 24333 | 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene | 4698-11-7 | C15H13NO | 详情 | 详情 |