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【结 构 式】

【分子编号】46717

【品名】6-[(4-chlorophenyl)(hydrazino)methyl]-1-methyl-1H-1,2,3-benzotriazole

【CA登记号】

【 分 子 式 】C14H14ClN5

【 分 子 量 】287.75156

【元素组成】C 58.44% H 4.9% Cl 12.32% N 24.34%

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:(VIII)

A scaleable process to produce vorozole has been reported: The reaction of 2,4-dichloronitrobenzene (I) with methylamine gives 5-chloro-N-methyl-2-nitroaniline (II), which is condensed with 4-chlorobenzonitrile (III) and oxidized with air to yield 4'-chloro-3-(methylamino)-4-nitrobenzophenone (IV). The hydrogenation of compound (IV), followed by cyclization by means of nitrous acid and reduction of the carbonyl group with NaBH4 affords the benzotriazole (V). Reaction of the OH group of (V) with SOCl2 provides the corresponding chloro derivative (VI), which is treated with acetohydrazide (VII) to give the racemic hydrazine derivative (VIII). Optical resolution of (VIII) by chiral chromatography yields the (S)-isomer (IX), which is finally cyclized with formamidine to afford vorozole.

1 De Knaep, A.G.M.; Vandendriessche, A.M.J.; Daemen, D.J.E.; et al.; Development summary towards a manufacturable process for R 83842 [(S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole]. Org Process Res Dev 2000, 4, 3, 162.
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) 21787 2,4-dichloro-1-nitrobenzene 611-06-3 C6H3Cl2NO2 详情 详情
(II) 46715 5-chloro-N-methyl-2-nitroaniline; N-(5-chloro-2-nitrophenyl)-N-methylamine 35966-84-8 C7H7ClN2O2 详情 详情
(III) 27360 4-chlorobenzonitrile 623-03-0 C7H4ClN 详情 详情
(IV) 46716 (4-chlorophenyl)[3-(methylamino)-4-nitrophenyl]methanone C14H11ClN2O3 详情 详情
(V) 14734 (4-chlorophenyl)(1-methyl-1H-1,2,3-benzotriazol-6-yl)methanol C14H12ClN3O 详情 详情
(VI) 14735 6-[chloro(4-chlorophenyl)methyl]-1-methyl-1H-1,2,3-benzotriazole C14H11Cl2N3 详情 详情
(VII) 29262 acetohydrazide 1068-57-1 C2H6N2O 详情 详情
(VIII) 46717 6-[(4-chlorophenyl)(hydrazino)methyl]-1-methyl-1H-1,2,3-benzotriazole C14H14ClN5 详情 详情
(IX) 46718 6-[(S)-(4-chlorophenyl)(hydrazino)methyl]-1-methyl-1H-1,2,3-benzotriazole C14H14ClN5 详情 详情
(X) 15369 Iminoformamide; Methanimidamide 463-52-5 CH4N2 详情 详情
Extended Information