【结 构 式】 |
【分子编号】51411 【品名】2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)-1-pyridiniumolate 【CA登记号】 |
【 分 子 式 】C9H9ClF3NO2 【 分 子 量 】255.6239096 【元素组成】C 42.29% H 3.55% Cl 13.87% F 22.3% N 5.48% O 12.52% |
合成路线1
该中间体在本合成路线中的序号:(II)The chlorination of 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine-N-oxide (I) with trichloroisocyanuric acid in hot chloroform gives the 2-chloromethyl derivative (II), which is condensed with 2-mercapto-1H-benzimidazole (III) by means of NaOH in methanol to yield the adduct (IV). The reaction of (IV) with PCl3 and acetic acid eliminates the N-oxide group, affording the sulfanylmethylpyridine (V). Finally, this compound is oxidized with tert-butyl hydroperoxide (VI) in ethanol to provide the target sulfoxide. Alternatively, the intermediate adduct (IV) can also be obtained as follows: The chlorination of 2,3-dimethyl-4-nitropyridine-N-oxide (VII) with trichloroisocyanuric acid as before gives the chloromethyl derivative (VIII), which is condensed with 2-mercapto-1H-benzimidazole (III) as before to yield the adduct (IX). Finally, this compound is treated with 2,2,2-trifluoroethanol (X), benzyltrimethylammonium chloride and K2CO3 in acetonitrile to afford the target intermediate (IV).
【1】 Montserrat Vidal, C.; Serra Macia, X. (Laboratorios Salvat SA); Intermediate for the synthesis of lansoprazole and process for obtaining it. ES 2063705 . |
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) | 19484 | 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-1-pyridiniumolate | C9H10F3NO2 | 详情 | 详情 | |
(II) | 51411 | 2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)-1-pyridiniumolate | C9H9ClF3NO2 | 详情 | 详情 | |
(III) | 12821 | 2-Mercaptobenzinidiazole; 1H-Benzimidazol-2-ylhydrosulfide; 1H-Benzimidazole-2-thiol; 2-Benzimidazolethiol; o-Phenylenethiourea; 2-Benzimidazolinethione; 1,3-Dihydro-2H-benzimidazole-2-thione | 583-39-1 | C7H6N2S | 详情 | 详情 |
(IV) | 51412 | 2-[(1H-benzimidazol-2-ylsulfanyl)methyl]-3-methyl-4-(2,2,2-trifluoroethoxy)-1-pyridiniumolate | C16H14F3N3O2S | 详情 | 详情 | |
(V) | 19488 | 2-[(1H-benzimidazol-2-ylsulfanyl)methyl]-3-methyl-4-pyridinyl 2,2,2-trifluoroethyl ether; 2-([[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfanyl)-1H-benzimidazole | 103577-40-8 | C16H14F3N3OS | 详情 | 详情 |
(VI) | 37518 | tert-butyl hydroperoxide | 75-91-2 | C4H10O2 | 详情 | 详情 |
(VII) | 19482 | 2,3-dimethyl-4-nitro-1-pyridiniumolate | 37699-43-7 | C7H8N2O3 | 详情 | 详情 |
(VIII) | 51413 | 2-(chloromethyl)-3-methyl-4-nitro-1-pyridiniumolate | C7H7ClN2O3 | 详情 | 详情 | |
(IX) | 51414 | 2-[(1H-benzimidazol-2-ylsulfanyl)methyl]-3-methyl-4-nitro-1-pyridiniumolate | C14H12N4O3S | 详情 | 详情 | |
(X) | 19483 | 2,2,2-trifluoro-1-ethanol | 75-89-8 | C2H3F3O | 详情 | 详情 |