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【结 构 式】

【分子编号】49491

【品名】1,3-dichloro-5-methylbenzene

【CA登记号】

【 分 子 式 】C7H6Cl2

【 分 子 量 】161.03004

【元素组成】C 52.21% H 3.76% Cl 44.03%

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:(XIV)

Alternatively, the target compound can be obtained as follows: Condensation between 2,6-dichloro-4-methylbenzonitrile (X) and 4-chloroiodobenzene (XI) by means of Mg in refluxing ether gives methyleneimine derivative (XII), which is then converted into 4-(4-chlorobenzoyl)-3,5-dichlorotoluene (XIII) by refluxing in dioxane-aqueous phosphate buffer. (Alternatively, compound (XIII) can also be obtained either by condensation of 3,5-dichlorotoluene (XIV) with p-chlorobenzoyl chloride (IV) by means of BuLi in THF or by treatment of 2,6-dichloro-4-methylbenzoic acid (XV) with thionyl chloride (SOCl2) in refluxing DMF to give (XVI), which then reacts with chlorobenzene (XVII) by means of AlCl3 in refluxing CCl4). Bromination of (XIII) is then performed by reaction with N-bromosuccinimide and dibenzoyl peroxide in refluxing benzene to give 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl bromide (XVIII). (Alternatively, (XVIII) can also be synthesized by treatment of the already reported benzophenone derivative (V) with HOAc in THF/H2O followed by reaction with phosphorus tribromide in diethyl ether.) Finally, (XVIII) is converted into the desired compound either by treatment with 5-amino-1,2,3-triazole-4-carboxamide (XIX) by means of NaH in refluxing EtOH or by first reaction of (XVIII) with KN3 in refluxing EtOH to furnish benzyl azide (VIII), followed by reaction with cyanoacetamide (IX) and NaOMe in refluxing EtOH.

1 Bochis, R.J.; Chabala, J.C.; Fisher, M.H. (Merck & Co., Inc.); 5-(Amino or substd.amino)-1,2,3-triazoles. EP 0151529; JP 1985188376; US 4590201 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 10295 p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride 122-01-0 C7H4Cl2O 详情 详情
(V) 49484 [4-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2,6-dichlorophenyl](4-chlorophenyl)methanone C20H23Cl3O2Si 详情 详情
(VIII) 49487 [4-(azidomethyl)-2,6-dichlorophenyl](4-chlorophenyl)methanone C14H8Cl3N3O 详情 详情
(IX) 12122 Cyanoacetamide; 2-Cyanoacetamide 107-91-5 C3H4N2O 详情 详情
(X) 49488 2,6-dichloro-4-methylbenzonitrile C8H5Cl2N 详情 详情
(XI) 19395 1-chloro-4-iodobenzene 637-87-6 C6H4ClI 详情 详情
(XII) 49489 (4-chlorophenyl)(2,6-dichloro-4-methylphenyl)methanimine C14H10Cl3N 详情 详情
(XIII) 49490 (4-chlorophenyl)(2,6-dichloro-4-methylphenyl)methanone C14H9Cl3O 详情 详情
(XIV) 49491 1,3-dichloro-5-methylbenzene C7H6Cl2 详情 详情
(XV) 49492 2,6-dichloro-4-methylbenzoic acid C8H6Cl2O2 详情 详情
(XVI) 49493 2,6-dichloro-4-methylbenzoyl chloride C8H5Cl3O 详情 详情
(XVII) 10190 1-Chlorobenzene 108-90-7 C6H5Cl 详情 详情
(XVIII) 49494 [4-(bromomethyl)-2,6-dichlorophenyl](4-chlorophenyl)methanone C14H8BrCl3O 详情 详情
(XIX) 49495 5-amino-1H-1,2,3-triazole-4-carboxamide C3H5N5O 详情 详情
Extended Information