【结 构 式】 |
【分子编号】56867 【品名】1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene 【CA登记号】 |
【 分 子 式 】C9H7Cl2N5 【 分 子 量 】256.09368 【元素组成】C 42.21% H 2.76% Cl 27.69% N 27.35% |
合成路线1
该中间体在本合成路线中的序号:(VI)The reaction of 2,3-dichlorobenzoic acid (I) with oxalyl chloride in dichloromethane gives the acyl chloride (II), which is condensed with labeled copper cyanide (III) by means of KI in refluxing xylene to yield the 2,3-dichlorobenzoyl cyanide (IV). The condensation of (IV) with labeled aminoguanidine (V) by means of sulfuric acid in acetonitrile/water affords adduct (VI), which is finally cyclized by refluxing under the conditions of the preceding reaction to provide the target labeled diaminotriazine. The intermediate labeled copper cyanide (III) has been obtained by reaction of CuSO4 with labeled potassium cyanide (VII) and Na2S2O5 in hot water. The intermediate labeled aminoguanidine (V) has been obtained by methylation of thiourea (VIII) with dimethyl sulfate in boiling water to give S-methylisothiourea (IX), which is finally treated with hydrazine (X) and NaOH in water.
【1】 Manning, C.O.; et al.; Synthesis of stable isotopically labelled versions of lamotrigine and its methylated metabolite. J Label Compd Radiopharm 2002, 45, 7, 611. |
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) | 24007 | 2,3-dichlorobenzoic acid | 50-45-3 | C7H4Cl2O2 | 详情 | 详情 |
(II) | 24008 | 2,3-dichlorobenzoyl chloride | 2905-60-4 | C7H3Cl3O | 详情 | 详情 |
(III) | 56856 | Copper (I) cyanide; Cuprous cyanide | 544-92-3 | CCuN | 详情 | 详情 |
(III) | 56861 | cyanocopper | CCuN | 详情 | 详情 | |
(IV) | 24009 | 2-(2,3-dichlorophenyl)-2-oxoacetonitrile; 2,3-Dichlorobenzoylcyanide | 77668-42-9 | C8H3Cl2NO | 详情 | 详情 |
(IV) | 56862 | 2-(2,3-dichlorophenyl)-2-oxoacetonitrile | C8H3Cl2NO | 详情 | 详情 | |
(V) | 56857 | CH6N4 | 详情 | 详情 | ||
(V) | 56866 | CH6N4 | 详情 | 详情 | ||
(VI) | 56858 | 1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene | C9H7Cl2N5 | 详情 | 详情 | |
(VI) | 56867 | 1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene | C9H7Cl2N5 | 详情 | 详情 | |
(VII) | 56859 | Potassium cyanide | 151-50-8 | CKN | 详情 | 详情 |
(VII) | 56860 | cyanopotassium | CKN | 详情 | 详情 | |
(VIII) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(VIII) | 56863 | thiourea | CH4N2S | 详情 | 详情 | |
(IX) | 10272 | [[Amino(imino)methyl]sulfanyl]methane | 2986-19-8 | C2H6N2S | 详情 | 详情 |
(IX) | 56864 | {[amino(imino)methyl]sulfanyl}methane | C2H6N2S | 详情 | 详情 | |
(X) | 27344 | hydrazine | 302-01-2 | H4N2 | 详情 | 详情 |
(X) | 56865 | hydrazine | H4N2 | 详情 | 详情 |