Yaozh News Star Club Edu TOP100 Customer Service APP
Iphone Download Android Download
  • English
  • 简体中文
Login Register
Search
Current Location： Home > Feedback Help Print

【结 构 式】

【分子编号】24333

【品名】10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene

【CA登记号】4698-11-7

【 分 子 式 】C15H13NO

【 分 子 量 】223.27436

【元素组成】C 80.69% H 5.87% N 6.27% O 7.17%
与该中间体有关的原料药合成路线共 9 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9

合成路线1

该中间体在本合成路线中的序号：(I)

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.

参考文献 中间体
合成目标
【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：(I)

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.

参考文献 中间体
合成目标
【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.
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

合成路线3

该中间体在本合成路线中的序号：(I)

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.

参考文献 中间体
合成目标
【1】 Milanese, A.; A process for the preparation of 10-oxo-10,11-dihydro-5H-dibenzo(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) 24333 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene 4698-11-7 C15H13NO 详情 详情
(II) 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4

该中间体在本合成路线中的序号：(VI)

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.

参考文献 中间体
合成目标
【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5

该中间体在本合成路线中的序号：(IV)

　

参考文献 中间体
合成目标
【1】 Fuenfschilling PC, Zang W, Beutler U et al. 2005.A new Industrial Process for Oxcarbazepine. Org.Proc. Res. Dev.,9:272-277.
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) 69514 2-(2-(2-methoxy-2-oxo-1-phenylethyl)phenyl)acetic acid C17H16O4 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
(V) 24335 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide C16H14N2O2 详情 详情

合成路线6

该中间体在本合成路线中的序号：(II)

　

参考文献 中间体
合成目标
【1】 Banfi A, Bollini D, Serra M et al. 2005. Process for preparaing oxcarbazepine via chlorocarbonylation with triphosgene. WO 2005092862.
【2】 Milanese A. 2005. Process for the preparation of oxcarbazepine. EP 1600443.
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) 44149 bis(trichloromethyl) carbonate;Triphosgene 32315-10-9 C3Cl6O3 详情 详情
(II) 24333 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene 4698-11-7 C15H13NO 详情 详情

合成路线7

该中间体在本合成路线中的序号：(IV)

　

参考文献 中间体
合成目标
【1】 Ansari SK,Bhat R,Kulkarni AK, et al.2003.Process for preparation of 10-methoxycarbamazepine by reaction of 10-methoxyiminostilbene with cyanic acid in the presence of weak acid. EP 1302464.
【2】 Gutman D, Baidossi W. Method of preparation a 5H-dibenz[b,f]azepine-5-carboxamide. WO 2003106414.
【3】 Muthukumaran M, Natarajan M, Thennati R. 2005.Process for reparation of 10-oxo-10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide. WO 2005096709.
【4】 Parenky C, Chaturvedi R. 2005. Novel process for reparation of 10-oxo-10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide(oxcarbazepine) via intermedia, 10-methoxy-5H-dibenz[b,f]azepine-5-carbonyl chloride. WO 2005066133.
【5】 Schmieder van de Vondervoort L, Bouttemy S, Heu F, et al. 2003. Low temperature, high conversion, liquid-phase benzylic oxidation with dioxygen by metal/NHPI-catalyzed co-oxidation with benzaldehude. European Journal of Organic Chemistry, (3):578-589.
【6】 Sivakumar BV, Bhirud SB, Batchu C, et al.2005.Preparation of 5H-dibenz[b,f]azepinecarboxamides. US 2005203297.
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) 69525 Dibenz[b,f]azepine-5-carbonyl chloride;Iminostilbene carbonyl chloride；5-Chlorocarbonyl iminostilbene;5H-dibenzo[b,f]azepine-5-carbonyl chloride 33948-22-0 C15H10ClNO 详情 详情
(II) 69526 10,11-dibromo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride C15H10Br2ClNO 详情 详情
(III) 69527 methyl 10-bromo-5H-dibenzo[b,f]azepine-5-carboxylate C16H12BrNO2 详情 详情
(IV) 24333 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene 4698-11-7 C15H13NO 详情 详情

合成路线8

该中间体在本合成路线中的序号：(IV)

　

参考文献 中间体
合成目标
【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

合成路线9

该中间体在本合成路线中的序号：(VI)

　

参考文献 中间体
合成目标
【1】 Fuenfschilling P, Kaufmann D, Lohse O, et al.2001.Preparation of dibenzo[b,f] azepine derivatives. WO 2001056992.
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) 69531 2-(o-tolylamino)benzoic acid；2-(2-Methylanilino)benzoic acid;N-(2-Methylphenyl)anthranilic acid;N-(2-Tolyl)anthranilic acid;N-(o-Tolyl)anthranilic acid；N-(o-Methylphenyl)anthranilic acid; N-(2'-Methylphenyl)anthranilic acid; 16610-44-9 C14H13NO2 详情 详情
(II) 69532 N,N-dimethyl-2-(o-tolylamino)benzamide C16H18N2O 详情 详情
(III) 69533 methyl (2-(dimethylcarbamoyl)phenyl)(o-tolyl)carbamate C18H20N2O3 详情 详情
(IV) 69515 methyl 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxylate C16H13NO3 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
Extended Information