2-[(2-chloro-2-phenylethyl)amino]-1-ethanesulfenyl cyanide -Drug Synthesis Database

【结构式】

【分子编号】39502

【品名】2-[(2-chloro-2-phenylethyl)amino]-1-ethanesulfenyl cyanide

【CA登记号】

【分子式】C₁₁H₁₃ClN₂S

【分子量】240.7564

【元素组成】C 54.88% H 5.44% Cl 14.73% N 11.64% S 13.32%

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：(VI)

The reaction of beta-chloroethylamine (III) with ammonium thiocyanate (B) gives beta-aminoethylthiocyanate (IV), which is alkylated with alpha,beta-dichloroethylbenzene (V) in hot benzene yielding the secondary amine (VI). The cyclization of (VI) in hot aqueous NaOH affords racemic levamisole, which is finally resolved in its optical isomers through the d-10-camphorsulfonate or N-benzene (or p-toluene)sulfonyl-L-(+)-glutamic salt.

参考文献中间体

合成目标

【1】 Bullock, M.W.; DE 1645975 .
【2】 Dick, P.R.; Rombi, M.; FR 2183313 .
【3】 Castañer, J.; Hopkins, S.J.; Blancafort, P.; Serradell, M.N.; Levamisole hydrochloride. Drugs Fut 1979, 4, 6, 420.
【4】 US 3579530 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	39499	ammonium thiocyanate	1762-95-4	CH₄N₂S	详情	详情
(rac)-(XII)	39503	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole		C₁₁H₁₂N₂S	详情	详情
(III)	33455	2-chloro-1-ethanamine; 2-chloroethylamine		C₂H₆ClN	详情	详情
(IV)	39500	2-amino-1-ethanesulfenyl cyanide		C₃H₆N₂S	详情	详情
(V)	39501	1-(1,2-dichloroethyl)benzene	1074-11-9	C₈H₈Cl₂	详情	详情
(VI)	39502	2-[(2-chloro-2-phenylethyl)amino]-1-ethanesulfenyl cyanide		C₁₁H₁₃ClN₂S	详情	详情

Extended Information