2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole -Drug Synthesis Database

【结构式】

【分子编号】33273

【品名】2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole

【CA登记号】696-23-1

【分子式】C₄H₅N₃O₂

【分子量】127.10272

【元素组成】C 37.8% H 3.97% N 33.06% O 25.18%

与该中间体有关的原料药合成路线共 5 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5

合成路线1

该中间体在本合成路线中的序号：(II)

2-Methylimidazole (I) is converted into the bisulfate salt, and then nitrated by means of a sulfonitric mixture in Ac2O to produce 2-methyl-4-nitroimidazole (II) . In a variant of this procedure, 2-methylimidazole (I) is nitrated by using a ferric nitrate-tonsyl adduct in several solvents. Imidazole (II) is then regioselectively alkylated with boiling 2-chloroethanol to produce the title compound. Alternatively, the alkylation of (II) has been reported by treatment with ethylene oxide (III) under acidic conditions.

参考文献中间体

合成目标

【1】 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 .
【2】 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 .

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)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(II)	33273	2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole	696-23-1	C₄H₅N₃O₂	详情	详情
(III)	10393	Oxirane; Ethylene oxide	75-21-8	C₂H₄O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Alternatively, 2-methyl-4-nitroimidazole (I) is protected by acylation in hot acetic anhydride to give (II). Addition of ethylene oxide (III) to the N-acetyl imidazole (II) in the presence of SO3, followed by acidic hydrolysis furnishes the title compound

参考文献中间体

合成目标

【1】 Lavigne, M.; Mandard-Cazin, B. (Aventis Pharma SA); Process for preparing hydroxyalkyl-1 nitro-5 imidazoles. WO 9113877 .

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)	33273	2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole	696-23-1	C₄H₅N₃O₂	详情	详情
(II)	62361	(2-methyl-4-nitro-1H-imidazol-1-yl)methyl acetate		C₇H₉N₃O₄	详情	详情
(III)	10393	Oxirane; Ethylene oxide	75-21-8	C₂H₄O	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

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).

参考文献中间体

合成目标

【1】 Nouveaux derives de l'imidazole et compositions les contenant. FR 3270M .
【2】 Cosar, C.; Crisan, C.; Horclois, R.; Jacob, R.M.; Robert, J.; Tchelitcheff, S.; Vaupre,R.; Nitroimidazoles. Arzneim-Forsch Drug Res 1966, 16, 1, 23-29.
【3】 Hillier, K.; Secnidazole. Drugs Fut 1979, 4, 4, 280.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	24485	Propylene oxide; 2-Methyloxirane		C₃H₆O	详情	详情
(B)	33274	1-chloro-2-propanol; 1-chloroisopropanol	127-00-4	C₃H₇ClO	详情	详情
(I)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(II)	33273	2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole	696-23-1	C₄H₅N₃O₂	详情	详情

合成路线4

该中间体在本合成路线中的序号： (III)

参考文献中间体

合成目标

【1】藏立言．2004．瞢确唑的翻备方法．发明专利申请公开说明书，CN 1475484

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	33273	2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole	696-23-1	C₄H₅N₃O₂	详情	详情
(I)	23712	1-ethanethiol; ethylhydrosulfide	75-08-1	C₂H₆S	详情	详情
(II)	66849	2-(ethylthio)ethanol；2-hydroxyethyl ethyl sulfide	110-77-0	C₄H₁₀OS	详情	详情
(IV)	66850	1-(2-(ethylthio)ethyl)-2-methyl-5-nitro-1H-imidazole		C₈H₁₃N₃O₂S	详情	详情

合成路线5

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】童小兵，吕建国，姜维斌，等．2005．瞢硝睦的制备方法，发明专利申请公开说明书，CN 1706832

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)	66849	2-(ethylthio)ethanol；2-hydroxyethyl ethyl sulfide	110-77-0	C₄H₁₀OS	详情	详情
(II)	33273	2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole	696-23-1	C₄H₅N₃O₂	详情	详情
(III)	66850	1-(2-(ethylthio)ethyl)-2-methyl-5-nitro-1H-imidazole		C₈H₁₃N₃O₂S	详情	详情

Extended Information