【结 构 式】 |
【分子编号】14731 【品名】(1-methyl-1H-1,2,3-benzotriazol-6-yl)methanol 【CA登记号】 |
【 分 子 式 】C8H9N3O 【 分 子 量 】163.17908 【元素组成】C 58.88% H 5.56% N 25.75% O 9.8% |
合成路线1
该中间体在本合成路线中的序号:(V)The reaction of 3-chloro-4-nitrobenzoic acid (I) with methylamine gives 3-(methylamino)-4-nitrobenzoic acid (II), which is hydrogenated in the presence of Raney Nickel to yield 4-amino-3-(methylamino)benzoic acid (III). Treatment of compound (III) with sodium nitrite affords 1-methyl-1H-benzotriazole-6-carboxylic acid (IV), which is reduced with lithium aluminum hydride in THF to give 6-(hydroxymethyl)-1-methyl-1H-benzotriazole (V). Oxidation of (V) with potassium permanganate in dichloroethane yields 1-methyl-1H-benzotriazole-6-carboxaldehyde (VI), which on treatment with the Grignard reagent derived from 1-bromo-4-chlorobenzene (VII) gives 6-(4-chloro-alpha-hydroxybenzyl)-1-methyl-1H-benzotriazole (VIII). Treatment of compound (VIII) with thionyl chloride in THF yields 6-(alpha,4-dichlorobenzyl)-1-methyl-1H-benzotriazole (IX), which is finally condensed with 1,2,4-triazole (X) and sodium hydride in DMF.
【1】 Raeymaekers, A.H.M.; Freyne, E.J.E.; Van Gelder, J.L.H.; Vener, M.G. (Janssen Pharmaceutica NV); (1H-Arol-1-ylmethyl)substd. Benzotriazole derivatives. AU 8816537; EP 0293978; JP 1988316775 . |
【2】 Graul, A.; Prous, J.; Castaner, J.; Vorozole. Drugs Fut 1994, 19, 5, 457. |
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) | 14727 | 3-chloro-4-nitrobenzoic acid | C7H4ClNO4 | 详情 | 详情 | |
(II) | 14728 | 3-(methylamino)-4-nitrobenzoic acid | C8H8N2O4 | 详情 | 详情 | |
(III) | 14729 | 4-amino-3-(methylamino)benzoic acid | C8H10N2O2 | 详情 | 详情 | |
(IV) | 14730 | 1-methyl-1H-1,2,3-benzotriazole-6-carboxylic acid | C8H7N3O2 | 详情 | 详情 | |
(V) | 14731 | (1-methyl-1H-1,2,3-benzotriazol-6-yl)methanol | C8H9N3O | 详情 | 详情 | |
(VI) | 14732 | 1-methyl-1H-1,2,3-benzotriazole-6-carbaldehyde | C8H7N3O | 详情 | 详情 | |
(VII) | 14733 | 4-Bromochlorobenzene; 1-bromo-4-chlorobenzene | 106-39-8 | C6H4BrCl | 详情 | 详情 |
(VIII) | 14734 | (4-chlorophenyl)(1-methyl-1H-1,2,3-benzotriazol-6-yl)methanol | C14H12ClN3O | 详情 | 详情 | |
(IX) | 14735 | 6-[chloro(4-chlorophenyl)methyl]-1-methyl-1H-1,2,3-benzotriazole | C14H11Cl2N3 | 详情 | 详情 | |
(X) | 13135 | 1H-1,2,4-Triazole; 1,2,4-Triazole | 288-88-0 | C2H3N3 | 详情 | 详情 |