benzyl ethanimidothioate -Drug Synthesis Database

【结构式】

【分子编号】19172

【品名】benzyl ethanimidothioate

【CA登记号】

【分子式】C₉H₁₁NS

【分子量】165.25908

【元素组成】C 65.41% H 6.71% N 8.48% S 19.4%

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 m-xylenediamine (I) with triethylamine and di-tert-butyldicarbonate (II) gives the corresponding tert-butyl N-[3-(aminomethyl)benzyl] carbamate hydrochloride (III), which is converted into the tert-butyl N-[3-((acetimidoyl)aminomethyl]benzyl) carbamate hydrochloride (VII) by reaction with S-benzylthioacetimidate hydrochloride (VI). This intermediate (VI) could be obtained by reaction of thioacetamide (IV) with benzyl chloride (V). Finally, compound (VII) is deprotected with HCl to afford the corresponding N-[3-(aminomethyl)benzyl] acetamidine hydrochloride.

参考文献中间体

合成目标

【1】 Itabashi, K.; Takido, T.; An efficient synthesis of unsymmetrical sulfides using liquid-liquid phase transfer catalysis. Synthesis 1987, 817.
【2】 Oplinger, J.A.; Garvey, E.P.; Furfine, E.S.; Shearer, B.G.; Collins, J.L. (Glaxo Wellcome plc); Acetamidine derivs. and their use as inhibitors for the nitric oxide synthase. EP 0799191; JP 1999500711; US 5866612; WO 9619440 .

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)	19167	3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine	1477-55-0	C₈H₁₂N₂	详情	详情
(II)	13214	Di-tert-butyldicarbonate; Dicarbonic acid bis(1,1-dimethylethyl) ester; dicarbonic acid di-tert-butyl ester pyrocarbonic acid di-tert-butyl ester; bis(1,1-dimethylethyl) dicarbonate di-tert-butyl pyrocarbonate	24424-99-5	C₁₀H₁₈O₅	详情	详情
(III)	19169	tert-butyl N-[3-(aminomethyl)benzyl]carbamate; tert-butyl 3-(aminomethyl)benzylcarbamate	108467-99-8	C₁₃H₂₀N₂O₂	详情	详情
(IV)	19170	ethanethioamide	62-55-5	C₂H₅NS	详情	详情
(V)	19171	1-(Chloromethyl)benzene; Benzyl chloride	100-44-7	C₇H₇Cl	详情	详情
(VI)	19172	benzyl ethanimidothioate		C₉H₁₁NS	详情	详情
(VII)	19173	tert-butyl 3-[(ethanimidoylamino)methyl]benzylcarbamate		C₁₅H₂₃N₃O₂	详情	详情

Extended Information