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【结 构 式】 
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【分子编号】48673 【品名】10H-Dibenz[b,f]azepin-10-one,5,11-dihydro-;10-Oxo-10,11-Dihydro-5H-dibenz[b,f]azepine;5,11-dihydro-10H-dibenzo[b,f]azepin-10-one 【CA登记号】21737-58-6 |
【 分 子 式 】C14H11NO 【 分 子 量 】209.24748 【元素组成】C 80.36% H 5.3% N 6.69% O 7.65% |
合成路线1
该中间体在本合成路线中的序号：(XII)Finally, deprotection of either intermediate (V) with TMS-Cl and NaI, intermediate (VIII) with TiCl4 or intermediate (XI) with Rh(PPh3)3Cl give, in all cases, 10,11-dihydro-5H-dibenz[b,f]azepin-10-one (XII), which is finally treated with chlorosulfonyl isocyanate to afford oxcarbazepine.
| 【1】 Lohse, O.; Kaufmann, D.; France, J.; Beutler, U.; Funfschilling, P.; Zaugg, W.; Furet, P.; New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives. Tetrahedron Lett 2001, 42, 3, 385. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 48665 | 5-benzyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one | C21H17NO | 详情 | 详情 | |
| (VIII) | 48669 | 5-(4-methoxybenzyl)-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one | C22H19NO2 | 详情 | 详情 | |
| (XI) | 48672 | 5-allyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one | C17H15NO | 详情 | 详情 | |
| (XII) | 48673 | 10H-Dibenz[b,f]azepin-10-one,5,11-dihydro-;10-Oxo-10,11-Dihydro-5H-dibenz[b,f]azepine;5,11-dihydro-10H-dibenzo[b,f]azepin-10-one | 21737-58-6 | C14H11NO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)This compound has been obtained by two related ways: 1. The hydrolysis of 10-methoxy-5H-dibenzo[b,f]azepine (I) with refluxing 2N HCl gives 10,11-dihydro-5H-dibenzo[b,f]azepin-5-one (II), which is then treated with chlorosulfonyl isocyanate in chloroform to yield the target carboxamide. 2. The reaction of 10-methoxy-5H-dibenzo[b,f]azepine (I) with potassium cyanate in hot sulfuric acid also gives the target carboxamide. In this reaction sodium cyanate can also be used instead of the potassium salt. Other strong acids such as trichloroacetic acid or anhydrous HCl in acetic acid can be used instead of sulfuric acid.
| 【1】 Milanese, A.; A process for the preparation of 10-oxo-10,11-dihydro-5H-dibenzo(b,f)azepin-5-carboxamide. WO 9621649 . |
合成路线3
该中间体在本合成路线中的序号：(I)
| 【1】 Alsters P, Bouttemy S. 2000. Process for the oxidation of substrates containing methyl, methylene, or methine groups. EP 1004566. |
| 【2】 Che DQ, Corelli-Rennie N, Guntoori BR, et al. 2005. Process for the preparation of oxcarbazepine and related intermediates. US 2005282797 |
| 【3】 Milanese A.1996.Preparatuon of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepin-5-carboxamide. WO 9621649 |
| 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) | 48673 | 10H-Dibenz[b,f]azepin-10-one,5,11-dihydro-;10-Oxo-10,11-Dihydro-5H-dibenz[b,f]azepine;5,11-dihydro-10H-dibenzo[b,f]azepin-10-one | 21737-58-6 | C14H11NO | 详情 | 详情 |
| (II) | 69521 | (10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl)sulfamoyl chloride | C15H11ClN2O4S | 详情 | 详情 |