4-(propylsulfanyl)-1,2-benzenediamine; 2-amino-4-(propylsulfanyl)phenylamine; 2-Amino-5-propylthioaniline -Drug Synthesis Database

【结构式】

【分子编号】33598

【品名】4-(propylsulfanyl)-1,2-benzenediamine; 2-amino-4-(propylsulfanyl)phenylamine; 2-Amino-5-propylthioaniline

【CA登记号】66608-52-4

【分子式】C₉H₁₄N₂S

【分子量】182.28964

【元素组成】C 59.3% H 7.74% N 15.37% S 17.59%

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：(III)

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.

参考文献中间体

合成目标

【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

Extended Information