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【结 构 式】 
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【分子编号】29839 【品名】1-[[2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-1H-1,2,4-triazole 【CA登记号】86386-76-7 |
【 分 子 式 】C11H9F2N3O 【 分 子 量 】237.2088864 【元素组成】C 55.7% H 3.82% F 16.02% N 17.71% O 6.74% |
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：(VII)The Friedel-Crafts' condensation of 1,3-difluorobenzene (I) with chloroacetyl chloride (II) by means of AlCl3 yields alpha-chloro-2,4-difluoroacetophenone (III), which is treated with 1,2,4-triazole (IV) and triethylamine in refluxing ethyl acetate giving alpha-(1H-12,4-triazol-1-yl)-2,4-diftuoroacetophenone (V). The reaction of (V) with trimethylsulfoxonium iodide (VI) by means of NaOH in toluene affords 1-[2-(2,4-di fluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole (VII), which is finally treated again with 1,2,4-triazole (IV) and K2CO3 in hot DMF.
| 【1】 Narayanaswami, S.; Richardson, K. (Pfizer Inc.); Triazole antifungal agents. EP 0096569; ES 523038 . |
| 【2】 Richardson, K. (Pfizer Inc.); Triazoles. GB 2099818; US 4404216 . |
| 【3】 Fromtling, R.A.; Castaner, J.; Serradell, M.N.; Fluconazole. Drugs Fut 1985, 10, 12, 982. |
| 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) | 13095 | m-Difluorobenzene; 1,3-Difluorobenzene | 372-18-9 | C6H4F2 | 详情 | 详情 |
| (II) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
| (III) | 16321 | 2-Chloro-2',4'-difluoroacetophenone; 2-Chloro-1-(2,4-difluorophenyl)-1-ethanone | 51336-94-8 | C8H5ClF2O | 详情 | 详情 |
| (IV) | 13135 | 1H-1,2,4-Triazole; 1,2,4-Triazole | 288-88-0 | C2H3N3 | 详情 | 详情 |
| (V) | 15372 | 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone; 2,4-Difluoro-alpha-(1H-1,2,4-triazolyl)acetophenone | 863867-75-6 | C10H7F2N3O | 详情 | 详情 |
| (VI) | 29693 | Trimethylsulfoxonium iodide | 1774-47-6 | C3H9IOS | 详情 | 详情 |
| (VII) | 29839 | 1-[[2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-1H-1,2,4-triazole | 86386-76-7 | C11H9F2N3O | 详情 | 详情 |
Extended Information