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【结 构 式】 
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【药物名称】Amoscanate 【化学名称】N-(4-Isothiocyanatophenyl)-N-(4-nitrophenyl)amine 【CA登记号】26328-53-0 【 分 子 式 】C13H9N3O2S 【 分 子 量 】271.29958 |
【开发单位】 【药理作用】 |
合成路线1
Two new syntheses for amoscanate have been described: 1) The reaction of 4-isothiocyanatobenzoyl chloride (I) with sodium azide (II) gives 4-isothiocyanatobenzoyl azide (III), which by heating in chlorobenzene is converted into 4-isothiocyanatophenyl isocyanate (IV). Finally this compound is condensed with 4-nitrophenol (V) by heating at 190 C. 2) By condensation of 1,4-phenylenebisisothiocyanate (VI) with 4-nitrophenol (V) at 190 C as before.
| 【1】 IN 150073 . |
| 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) | 60780 | 4-isothiocyanatobenzoyl chloride | C8H4ClNOS | 详情 | 详情 | |
| (III) | 60781 | 4-isothiocyanatobenzoyl azide | C8H4N4OS | 详情 | 详情 | |
| (IV) | 60782 | 1-isocyanato-4-isothiocyanatobenzene; 4-isothiocyanatophenyl isocyanate | C8H4N2OS | 详情 | 详情 | |
| (V) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
| (VI) | 60783 | 1,4-diisothiocyanatobenzene; 4-isothiocyanatophenyl isothiocyanate | C8H4N2S2 | 详情 | 详情 |
合成路线2
By reaction of 4-nitro-4'-aminodiphenylamine (I) with N,N-diethylthiocarbamoyl chloride (II), ammonium thiocyanate (III), thiophosgene (IV), or bis-(N,N-diethylthiocarbamoyl)disulfide (V) in the appropriate solvent
| 【1】 Castaner, J.; Bogan, J.A.; Amoscanate. Drugs Fut 1977, 2, 1, 10. |
| 【2】 Brenneisen,P.; et al. (Ciba Geigy Corp.); Nuclear receptor ligands and ligand binding domains. DE 1932690; DE 1935338; US 3839582 . |