【结 构 式】 |
【分子编号】57673 【品名】2-[4-(trifluoromethyl)phenyl]-1H-imidazole-4-carbaldehyde 【CA登记号】 |
【 分 子 式 】C11H7F3N2O 【 分 子 量 】240.1846696 【元素组成】C 55.01% H 2.94% F 23.73% N 11.66% O 6.66% |
合成路线1
该中间体在本合成路线中的序号:(V)1,1-Dibromo-3,3,3-trifluoroacetone (I) is treated with a hot aqueous solution of sodium acetate, and subsequently condensed with 4-(trifluoromethyl)benzaldehyde (II) in the presence of ammonium hydroxide to furnish the trifluoromethyl imidazole (III). The imidazole trifluoromethyl group of (III) is then selectively converted to nitrile (IV) upon heating with a methanolic solution of ammonium hydroxide. Reduction of the cyano group of (IV) employing DIBAL in cold THF leads to aldehyde (V). This is finally converted to the target nitrone by condensation with N-tert-butyl hydroxylamine.
【1】 Dhainaut, A.; et al.; Synthesis, structure, and neuroprotective properties of novel imidazolyl nitrones. J Med Chem 2000, 43, 11, 2165. |
【2】 Dhainaut, A.; Lestage, P.; Lockhart, B.; Tizot, A.; Goldstein, S. (ADIR et Cie.); Nitrone derivs., process for their preparation and pharmaceutical compsns. containing them. CA 2274621; EP 0967207; FR 2780404; JP 2000026428; US 6034250 . |
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) | 35450 | 3,3-dibromo-1,1,1-trifluoroacetone | 431-67-4 | C3HBr2F3O | 详情 | 详情 |
(II) | 13380 | 4-(Trifluoromethyl)benzaldehyde; alpha,alpha,alpha-Trifluoro-p-tolualdehyde | 455-19-6 | C8H5F3O | 详情 | 详情 |
(III) | 57671 | 4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]-1H-imidazole | C11H6F6N2 | 详情 | 详情 | |
(IV) | 57672 | 2-[4-(trifluoromethyl)phenyl]-1H-imidazole-4-carbonitrile | C11H6F3N3 | 详情 | 详情 | |
(V) | 57673 | 2-[4-(trifluoromethyl)phenyl]-1H-imidazole-4-carbaldehyde | C11H7F3N2O | 详情 | 详情 |