【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% |
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 |