Parconazole, R-39500
帕康唑Chemical Name: 1-[2(S)-(2,4-Dichlorophenyl)-4(R)-(2-propynyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole
CAS No. 61400-59-7, 62973-77-7 (hydrochloride)
项目整合开发状态: Not Determined
项目研究机构:
合成路线:The cyclization of glycerol (I) with 2,4-dichlorophenacyl bromide (II) by means of p-toluenesulfonic acid in a refluxing mixture of toluene and butanol gives 2-bromomethyl-2-(2,4-dichlorophenyl)-4-(hydroxymethyl)-1,3-dioxolane (III),which by esterification with benzoyl chloride (IV) in pyridine followed by a fractionated crystallization affords cis-2-bromomethyl-2-(2,4-dichlorophenyl)-4-(benzoyloxymehyl)-3-dioxolane (V).The hydrolysis of (V) with NaOH in refluxing dioxane - water yields the corresponding alcohol (VI),which by reaction with imidazole (VII) by means of KI in refluxing dimethylacetamide gives cis-2-(1H-imidazol-1-ylmethyl)-2-(2,4-dichlorophenyl)-4-(hydroxymethyl)-1,3-dioxolane (VIII).Finally this compound is condensed with 3-chloro-1-propyn (IX) by means of NaH in DMF.
📌 参考资料/链接:
参考文献标题:
文献作者:Heeres,J.
参考来源:BE 837831; DE 2602770; FR 2298328; NL 7514381; US 3936470
📄 详细内容
合成路线:The cyclization of glycerol (I) with 2,4-dichlorophenacyl bromide (II) by means of p-toluenesulfonic acid in a refluxing mixture of toluene and butanol gives 2-bromomethyl-2-(2,4-dichlorophenyl)-4-(hydroxymethyl)-1,3-dioxolane (III),which by esterification with benzoyl chloride (IV) in pyridine followed by a fractionated crystallization affords cis-2-bromomethyl-2-(2,4-dichlorophenyl)-4-(benzoyloxymehyl)-3-dioxolane (V).The hydrolysis of (V) with NaOH in refluxing dioxane - water yields the corresponding alcohol (VI),which by reaction with imidazole (VII) by means of KI in refluxing dimethylacetamide gives cis-2-(1H-imidazol-1-ylmethyl)-2-(2,4-dichlorophenyl)-4-(hydroxymethyl)-1,3-dioxolane (VIII).Finally this compound is condensed with 3-chloro-1-propyn (IX) by means of NaH in DMF.
参考文献标题:Parconazole
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Arya,V.P.
参考来源:Drugs Fut 1979,4(7),513
产品链接: CAS No. 61400-59-7›› 产品链接: CAS No.62973-77-7››