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

【结 构 式】

【分子编号】29154

【品名】6-fluoro-4-[(1-phenylethyl)amino]-4-chromanecarbonitrile

【CA登记号】

【 分 子 式 】C18H17FN2O

【 分 子 量 】296.3442632

【元素组成】C 72.96% H 5.78% F 6.41% N 9.45% O 5.4%

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:(IV)

A new method for the synthesis of sorbinil has been reported: The condensation of 2,3-dihydro-6-fluoro-4H-1-benzopyran-4-one (I) with methylbenzylamine (II) by means of TiCl4 in benzene gives 2,3-dihydro-6-fluoro-4-(1-phenylethylimino)-4H-1-benzopyran (III), which by reaction with HCN in ethanol is converted to 4-cyano-2,3-dihydro-6-fluoro-4-(1-phenylethylamino)-4H-1-benzopyran (IV). The cyclization of (IV) with chlorosulfonyl isocyanate (V) in methylene chloride affords 2,3-dihydro-6-fluoro-3'-(1-phenylethyl)spiro(4H-1-benzopyran-4,4'-imidazolidine)-2',5'-dione (VI), which is finally treated with 48% HBr in refluxing acetic acid.

1 Kelbaugh, P.R.; Sarges, R.; Howard, H.R. Jr.; Synthesis of optically active spirohydantoins by asymmetric induction. Hydantoin formation from amino nitriles and chlorosulfonyl isocyanate. J Org Chem 1982, 47, 21, 4081-85.
2 Sarges, R. (Pfizer Inc.); Intermediates in the preparation of chiral hydantoins. US 4348526 .
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) 10056 6-Fluoro-2,3-dihydro-4H-chromen-4-one; 6-Fluoro-4-chromanone 66892-34-0 C9H7FO2 详情 详情
(II) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(III) 29153 N-(6-fluoro-2,3-dihydro-4H-chromen-4-ylidene)-1-phenyl-1-ethanamine C17H16FNO 详情 详情
(IV) 29154 6-fluoro-4-[(1-phenylethyl)amino]-4-chromanecarbonitrile C18H17FN2O 详情 详情
(V) 14101 Chlorosulfonyl isocyanate 1189-71-5 CClNO3S 详情 详情
(VI) 29155 (4S)-6-Fluoro-3'-(1-phenylethyl)-3,4-dihydro-2H-spiro[1-benzopyran-4-4'-imidazolidine]-2',5'-dione C19H17FN2O3 详情 详情
Extended Information