Reaction routes of Metronidazole
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Reaction routes of Metronidazole
sophia11 Mon Jul 18, 2011 9:05 pm
Metronidazole (CAS NO.443-48-1) is a prodrug. It is converted in anaerobic organisms by the redox enzyme pyruvate-ferredoxin oxidoreductase.
Metronidazole (CAS NO.: 443-48-1), with its chemical name of 2-Methyl-5-nitro-1H-imidazole-1-ethanol, could be produced through the following several reaction routes.
1). Preparation method one:
The title compound can also be obtained by alkylation, in different solvents, of 1-(acetoxymethyl)-2-methyl-4-nitroimidazole (I) with either ethylene sulfate (II) or with bis-(2-acetoxyethyl) sulfate (III) -generated from ethyleneglycol diacetate (IV) and either dimethyl sulfate or H2SO4 - followed by hydrolysis or alcoholysis treatment.
2). Preparation method two:
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-Metronidazole(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.
Metronidazole (CAS NO.: 443-48-1), with its chemical name of 2-Methyl-5-nitro-1H-imidazole-1-ethanol, could be produced through the following several reaction routes.
1). Preparation method one:
The title compound can also be obtained by alkylation, in different solvents, of 1-(acetoxymethyl)-2-methyl-4-nitroimidazole (I) with either ethylene sulfate (II) or with bis-(2-acetoxyethyl) sulfate (III) -generated from ethyleneglycol diacetate (IV) and either dimethyl sulfate or H2SO4 - followed by hydrolysis or alcoholysis treatment.
2). Preparation method two:
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-Metronidazole(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.
sophia11- Posts : 23
Join date : 2011-01-26
sophia11- Posts : 23
Join date : 2011-01-26
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