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【结 构 式】 
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【分子编号】34328 【品名】1-[[(2S,4S)-2-(2,4-dichlorophenyl)-4-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1,3-dioxolan-2-yl]methyl]-1H-imidazole 【CA登记号】 |
【 分 子 式 】C17H20Cl2N2O3S 【 分 子 量 】403.32888 【元素组成】C 50.63% H 5% Cl 17.58% N 6.95% O 11.9% S 7.95% |
合成路线1
该中间体在本合成路线中的序号：(IV)The acylation of 4-aminothiophenol (I) with ethyl chloroformate (II) is performed in a nitrogen atmosphere in the presence of NaHCO3 in CH2Cl2 / water medium giving ethyl (4-mercaptophenyl)carbamate (III). This compound is condensed with cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dixolan-4-yl]methyl methanesulfonate (IV) in the presence of K2CO3 in refluxing acetone under nitrogen, affording the title compound, which is converted to the monohydrochloride with i-PrOH / HCl in 4-methyl-2-pentanone.
| 【1】 Heeres, J.; Van der Veken, L.J.E.; Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives. DE 3166517D; EP 0052905 . |
| 【2】 Van Ginckel, R.; Geuens, G.; Heeres, J.; Tubulozole Hydrochloride. Drugs Fut 1984, 9, 12, 911. |
| 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) | 16490 | 4-aminophenylhydrosulfide; 4-aminothiophenol; 4-aminobenzenethiol | 1193-02-8 | C6H7NS | 详情 | 详情 |
| (II) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (III) | 13295 | ethyl 4-sulfanylphenylcarbamate | C9H11NO2S | 详情 | 详情 | |
| (IV) | 34328 | 1-[[(2S,4S)-2-(2,4-dichlorophenyl)-4-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1,3-dioxolan-2-yl]methyl]-1H-imidazole | C17H20Cl2N2O3S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Coupling of (IV) in a nitrogen atmosphere with 4-acetamidothiophenol (V) in refluxing acetone in the presence of K2CO3 affords cis-N-[4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethylthio]phenyl]acetamide, which is deacylated with NaOH in refluxing i-PrOH to give cis-4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl-methyl)-1,3-dioxolan-4-ylmethylthio]benzenamine (VII). This compound is converted with ethylchloroformate (II) into the title compound which is isolated as the monohydrochloride on treatment with i-PrOH / HCl.
| 【1】 Heeres, J.; Van der Veken, L.J.E.; Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives. DE 3166517D; EP 0052905 . |
| 【2】 Van Ginckel, R.; Geuens, G.; Heeres, J.; Tubulozole Hydrochloride. Drugs Fut 1984, 9, 12, 911. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (IV) | 34328 | 1-[[(2S,4S)-2-(2,4-dichlorophenyl)-4-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1,3-dioxolan-2-yl]methyl]-1H-imidazole | C17H20Cl2N2O3S | 详情 | 详情 | |
| (V) | 34329 | N-(4-sulfanylphenyl)acetamide | 1126-81-4 | C8H9NOS | 详情 | 详情 |
| (VI) | 34330 | N-[4-([[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl]sulfanyl)phenyl]acetamide | C22H21Cl2N3O3S | 详情 | 详情 | |
| (VII) | 34331 | 4-([[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl]sulfanyl)aniline; 4-([[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl]sulfanyl)phenylamine | C20H19Cl2N3O2S | 详情 | 详情 |