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【结 构 式】 
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【分子编号】29155 【品名】(4S)-6-Fluoro-3'-(1-phenylethyl)-3,4-dihydro-2H-spiro[1-benzopyran-4-4'-imidazolidine]-2',5'-dione 【CA登记号】 |
【 分 子 式 】C19H17FN2O3 【 分 子 量 】340.3540632 【元素组成】C 67.05% H 5.03% F 5.58% N 8.23% O 14.1% |
合成路线1
该中间体在本合成路线中的序号：(VI)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 |