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Secnidazole, RP-14539, PM-185184, Flagentyl

塞克硝唑Chemical Name: alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol; 1-(2-Hydroxypropyl)-2-methyl-5-nitroimidazole; 1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol
CAS No. 3366-95-8
项目整合开发状态: Launched
项目研究机构: Aventis Pharma (Originator)
合成路线:The condensation of (I) with propylene oxide (A) in ethanol at 20 C gives 1-(2-hydroxypropyl)-2-methylimidazole (III),which is acetylated with acetyl chloride in refluxing acetonitrile yielding the corresponding acetate (IV).The nitration of (IV) by means of HNO3 and P2O5 affords 1-(2-acetoxypropyl)-2-methyl-4-nitroimidazole (V),which is finally hydrolyzed with 4N HCl at 90 C.
📌 参考资料/链接:
参考文献标题:New process for the preparation of 5-nitroimidazole derivatives
文献作者:Jeanmart,C.; Messer,M.(Aventis Pharma SA)
参考来源:DE 2107405; FR 2079880; GB 1278757; JP 49080066

📄 详细内容


合成路线:The reaction of (I) with chloroacetone (C) by means of K2CO3 in refluxing acetone gives (2-methylimidazol-1-yl)acetone (VI),which is nitrated with HNO3 and P2O5 affording the corresponding nitro compound (VII).Finally,this product is reduced with NaBH4 in methanol at room temperature.

参考文献标题:Process for the preparation of 5-nitroimidazole derivatives
文献作者:Jeanmart,C.; Messer,M.(Aventis Pharma SA)
参考来源:CH 513177; DE 2107423; FR 2079879; GB 1278758; NL 7101641


合成路线:The nitration of (I) with HNO3 and H2SO4 gives 2-methyl-4(5)-nitroimidazole (II),which is then condensed with refluxing 1-chloroisopropanol (B) or with propylene oxide in 85% formic acid (A).

合成路线:The condensation of (I) with propylene oxide (A) in ethanol at 20 C gives 1-(2-hydroxypropyl)-2-methylimidazole (III),which is acetylated with acetyl chloride in refluxing acetonitrile yielding the corresponding acetate (IV).The nitration of (IV) by means of HNO3 and P2O5 affords 1-(2-acetoxypropyl)-2-methyl-4-nitroimidazole (V),which is finally hydrolyzed with 4N HCl at 90 C.

合成路线:The reaction of (I) with chloroacetone (C) by means of K2CO3 in refluxing acetone gives (2-methylimidazol-1-yl)acetone (VI),which is nitrated with HNO3 and P2O5 affording the corresponding nitro compound (VII).Finally,this product is reduced with NaBH4 in methanol at room temperature.

参考文献标题:Secnidazole
文献作者:Hillier,K.
参考来源:Drugs Fut 1979,4(4),280


合成路线:The nitration of (I) with HNO3 and H2SO4 gives 2-methyl-4(5)-nitroimidazole (II),which is then condensed with refluxing 1-chloroisopropanol (B) or with propylene oxide in 85% formic acid (A).

合成路线:The condensation of (I) with propylene oxide (A) in ethanol at 20 C gives 1-(2-hydroxypropyl)-2-methylimidazole (III),which is acetylated with acetyl chloride in refluxing acetonitrile yielding the corresponding acetate (IV).The nitration of (IV) by means of HNO3 and P2O5 affords 1-(2-acetoxypropyl)-2-methyl-4-nitroimidazole (V),which is finally hydrolyzed with 4N HCl at 90 C.

合成路线:The reaction of (I) with chloroacetone (C) by means of K2CO3 in refluxing acetone gives (2-methylimidazol-1-yl)acetone (VI),which is nitrated with HNO3 and P2O5 affording the corresponding nitro compound (VII).Finally,this product is reduced with NaBH4 in methanol at room temperature.

参考文献标题:Nitroimidazoles
文献作者:Cosar,C.; Crisan,C.; Horclois,R.; Jacob,R.M.; Robert,J.; Tchelitcheff,S.; Vaupr? R.
参考来源:Arzneim-Forsch Drug Res 1966,16(1),23-29


合成路线:The nitration of (I) with HNO3 and H2SO4 gives 2-methyl-4(5)-nitroimidazole (II),which is then condensed with refluxing 1-chloroisopropanol (B) or with propylene oxide in 85% formic acid (A).
参考文献标题:Nouveaux d閞iv閟 de l'imidazole et compositions les contenant
文献作者:
参考来源:FR 3270M


产品链接: CAS No. 3366-95-8››