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【结 构 式】

【分子编号】52655

【品名】2,3-Dichloronitrobenzene; 1,2-Dichloro-3-Nitrobenzene; Nitro-o-dichlorobenzene

【CA登记号】3209-22-1

【 分 子 式 】C6H3Cl2NO2

【 分 子 量 】192.00076

【元素组成】C 37.53% H 1.57% Cl 36.93% N 7.3% O 16.67%

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:(I)

Hydrogenation of 2,3-dichloronitrobenzene (I) with H2 over Ra-Ni in methanol gives 2,3-dichloroaniline (II), which is diazotized with NaNO2 and HCl and treated with CuCN to yield 2,3-dichlorobenzonitrile (III). Hydrolysis of the nitrile (III) with NaOH in refluxing methanol/water affords 2,3-dichlorobenzoic acid (IV), which is treated with hot SOCl2 to provide the corresponding acyl chloride (V). Reaction of (V) with CuCN and KI in refluxing chlorobenzene gives 2,3-dichlorobenzoyl cyanide (VI), which is condensed with aminoguanidine (VII) by means of H2SO4/TsOH in hot toluene to yield 2,3-dichlorobenzoyl cyanide amidinohydrazone (VIII). Finally, this compound is cyclized by treatment with NaOMe in refluxing methanol.

1 Srivastava, A.R.; Sasikumar, T.M.; Radhakrishnan, T.V. (RPG Life Sciences Ltd); A process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine. WO 0149669 .
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) 52655 2,3-Dichloronitrobenzene; 1,2-Dichloro-3-Nitrobenzene; Nitro-o-dichlorobenzene 3209-22-1 C6H3Cl2NO2 详情 详情
(II) 28562 2,3-dichlorophenylamine 608-27-5 C6H5Cl2N 详情 详情
(III) 30204 2,3-dichlorobenzonitrile 6574-97-6 C7H3Cl2N 详情 详情
(IV) 24007 2,3-dichlorobenzoic acid 50-45-3 C7H4Cl2O2 详情 详情
(V) 24008 2,3-dichlorobenzoyl chloride 2905-60-4 C7H3Cl3O 详情 详情
(VI) 24009 2-(2,3-dichlorophenyl)-2-oxoacetonitrile; 2,3-Dichlorobenzoylcyanide 77668-42-9 C8H3Cl2NO 详情 详情
(VII) 10015 1-Hydrazinecarboximidamide; Hydrazinecarboximidamide 79-17-4 CH6N4 详情 详情
(VIII) 52654 2-[cyano(phenyl)methylidene]-1-hydrazinecarboximidamide C9H9N5 详情 详情
Extended Information