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【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%

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:(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
Extended Information