• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】29089

【品名】N-(3-chlorophenyl)-2-(hydroxyimino)acetamide

【CA登记号】

【 分 子 式 】C8H7ClN2O2

【 分 子 量 】198.60856

【元素组成】C 48.38% H 3.55% Cl 17.85% N 14.1% O 16.11%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XII)

The reaction of 3-chloroaniline (X) with choral hydrate (XI) and hydroxylamine gives isonitroso-3-chloroacetanilide (XII), which is cyclized by means of H2SO4 to 4-chloroisatin (XIII). Chlorination of (XIII) with SO2Cl2 affords 4,5-dichloroisatin (XIV), which is oxidized with H2O2 yielding 5,6-dichloroanthranilic acid (XV). The reduction of (XV) with borane in THF gives 6-amino-2,3-dichlorobenzyl alcohol (XVI), which by reaction with SOCl2 in benzene is converted to 6-amino-2,3-dichlorobenzyl chloride (XVII). This compound is condensed with ethyl glycinate (XVIII) by means of triethylamine in refluxing methylene chloride to give ethyl N-(6-amino-2,3-dichlorobenzyl)glycinate (VII), which is cyclized with cyanogen bromide (VIII) in toluene affording ethyl 5,6-dichloro-3,4-dihydro-2-(1H)-iminoquinazoline-3-acetate (IX). Finally, this compound is submitted to a new cyclization by means of triethylamine in refluxing ethanol.

1 Jenks, T.A.; Beverung, W.N.Jr.; Partyka, R.A. (Bristol-Myers Squibb Co.); Preparation of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-one. CA 1137474 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 29087 ethyl 2-[(6-amino-2,3-dichlorobenzyl)amino]acetate C11H14Cl2N2O2 详情 详情
(VIII) 28017 cyanic bromide;cyanogen bromide 506-68-3 CBrN 详情 详情
(IX) 29088 ethyl 2-[5,6-dichloro-2-imino-1,4-dihydro-3(2H)-quinazolinyl]acetate C12H13Cl2N3O2 详情 详情
(X) 25239 3-chloroaniline; 3-chlorophenylamine 108-42-9 C6H6ClN 详情 详情
(XI) 14018 2,2,2-Trichloro-1,1-ethanediol; Chloral hydrate 302-17-0 C2H3Cl3O2 详情 详情
(XII) 29089 N-(3-chlorophenyl)-2-(hydroxyimino)acetamide C8H7ClN2O2 详情 详情
(XIII) 29090 4-chloro-1H-indole-2,3-dione C8H4ClNO2 详情 详情
(XIV) 29091 4,5-dichloro-1H-indole-2,3-dione C8H3Cl2NO2 详情 详情
(XV) 29092 6-amino-2,3-dichlorobenzoic acid C7H5Cl2NO2 详情 详情
(XVI) 29093 (6-amino-2,3-dichlorophenyl)methanol C7H7Cl2NO 详情 详情
(XVII) 29094 3,4-dichloro-2-(chloromethyl)aniline C7H6Cl3N 详情 详情
(XVIII) 10309 ethyl 2-aminoacetate; Glycine ethyl ester 459-73-4 C4H9NO2 详情 详情
Extended Information