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【结 构 式】 
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【药物名称】Albendazole, SK&F-62979, Albenza, Eskazole, Valbazen(Veterinary), Zentel 【化学名称】N-(5-Propylsulfanyl)benzimidazole-2-ylcarbamic acid methyl ester 【CA登记号】54965-21-8 【 分 子 式 】C12H15N3O2S 【 分 子 量 】265.33625 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Treatment of Helminthic Diseases |
合成路线1
The condensation of 3-chloro-6-nitroacetanilide (I) with propylmercaptane (A) by means of aqueous refluxing NaOH gives 2-nitro-5-propylthioaniline (II), which was reduced with H2 over Pd/C in ethanol HCl to yield 4-propylthio-o-phenylenediamine (III). The cyclization of (III) with cyanogen bromide affords 2-amino-5-propylthiobenzimidazole (IV), which is finally condensed with methyl chloroformate. It can be condensed directly with a mixture of cyanamide and methyl chloroformate or with carbomethoxycyanamide (B). All these condensations are performed in basic medium.
| 【1】 Gyurik, R.J.; Theodorides, V.J.; Methyl 5-propylthio-2-benzimidazolecarbamate. DE 2527065; FR 2275203; GB 1464326; JP 51012936; US 3915986 . |
| 【2】 Bogan, J.; Castaner, J.; Albendazole. Drugs Fut 1977, 2, 2, 81. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 23703 | propylhydrosulfide; 1-propanethiol | 107-03-9 | C3H8S | 详情 | 详情 |
| (B) | 33600 | methyl cyanocarbamate | C3H4N2O2 | 详情 | 详情 | |
| (I) | 25241 | N-(5-chloro-2-nitrophenyl)acetamide | 39163-92-3 | C8H7ClN2O3 | 详情 | 详情 |
| (II) | 33597 | 2-nitro-5-(propylsulfanyl)phenylamine; 2-nitro-5-(propylsulfanyl)aniline | C9H12N2O2S | 详情 | 详情 | |
| (III) | 33598 | 4-(propylsulfanyl)-1,2-benzenediamine; 2-amino-4-(propylsulfanyl)phenylamine; 2-Amino-5-propylthioaniline | 66608-52-4 | C9H14N2S | 详情 | 详情 |
| (IV) | 33599 | 5-(propylsulfanyl)-1H-benzimidazol-2-ylamine; 5-(propylsulfanyl)-1H-benzimidazol-2-amine | C10H13N3S | 详情 | 详情 |