Meobentine sulfate

N-(4-甲氧基苄)-N',N''-二甲基鸟苷半硫酸盐 甲氧苯汀 Chemical Name: N-(4-Methoxybenzyl)-N',N''-dimethylguanidine hemisulfate
CAS No. 58503-79-0, 46464-11-3 (free base)
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Compound can be prepared in three different ways all starting from 4-methoxybenzylamine (I) [prepared by methylation of 4-hydroxybenzonitrile (V) with dimethyl sulfate in aqueous NaOH to afford 4-methoxybenzonitrile (VI),which is then hydrogenated with H2 over Raney-Ni in ethanol]:1) By condensation of 4-methoxybenzylamine (I) with N,N',S-trimethylisothiourea hydroiodide (C) in refluxing ethanol,followed by treatment with H2SO4.2) By reaction of 4-methoxybenzylamine (I) with diethyl iminocarbonate (A) in water to give diethyl N-(4-methoxybenzyl)iminocarbonate (II),followed by treatment with methylamine in water - ethanol - H2SO4.3) By reaction of 4-methoxybenzylamine (I) with methyl isothiocyanate (B) in ether to yield N-(4-methoxybenzyl)-N'-methylthiourea (III),which is then methylated with MeI in refluxing methanol affording N-(4-methoxybenzyl)-N',S-dimethylisothiourea (IV).Finally,this compound is treated first with methylamine in refluxing methanol and then with H2SO4.