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【结 构 式】 
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【分子编号】22562 【品名】2-[(E)-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-propenoyl]-1-hydrazinecarbothioamide 【CA登记号】 |
【 分 子 式 】C13H13F4N3O2S 【 分 子 量 】351.3248528 【元素组成】C 44.44% H 3.73% F 21.63% N 11.96% O 9.11% S 9.13% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde (I) with refluxing acetic anhydride gives 3-[4-(2,2,3,3-tetrafluoropropoxy) phenyl]acrylic acid (II), which is treated with refluxing SOCl2 to yield the corresponding acid chloride (III). The reaction of (III) with thiosemicarbazide in toluene affords 3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]acryloylthiosemicarbazide (IV), which is cyclized by means of NaNO2 and HNO3 in water to give 3-[4-(2,2,3,3-tetrafluoropropoxy) styryl]-1,2,4-triazole (V). Finally, this compound is condensed with 2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)-1,2-epoxypropane (VI) by means of NaH in hot DMF.
| 【1】 Bayles, F.T.; Boyle, F.T.; Gravestock, M.B.; Wardleworth, J.M. (AstraZeneca plc); Antifungal azole cpds.. EP 0174769; US 4925863 . |
| 【2】 Prous, J.; Castaner, J.; ICI-195739 . Drugs Fut 1988, 13, 5, 408. |
| 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) | 15481 | 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde | C10H8F4O2 | 详情 | 详情 | |
| (II) | 15484 | (E)-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-propenoic acid | C12H10F4O3 | 详情 | 详情 | |
| (III) | 22561 | (E)-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-propenoyl chloride | C12H9ClF4O2 | 详情 | 详情 | |
| (IV) | 22562 | 2-[(E)-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-propenoyl]-1-hydrazinecarbothioamide | C13H13F4N3O2S | 详情 | 详情 | |
| (V) | 15476 | 2,2,3,3-tetrafluoropropyl 4-[(E)-2-(1H-1,2,4-triazol-3-yl)ethenyl]phenyl ether; 3-[(E)-2-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]ethenyl]-1H-1,2,4-triazole | C13H11F4N3O | 详情 | 详情 | |
| (VI) | 15477 | 1-[[(2R)-2-(2,4-difluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole | C11H9F2N3O | 详情 | 详情 |