2-Isopropyl-4-nitroimidazole

The 2-isopropyl-4-nitroimidazole derivative has N 1.53 mT. Rotational diffusion study at several temperatures. 

Isopropyl-4(or 5-nitroimidazole) (31 g = 0.2 mol), dioxane (70 g) and dimethylsulfate (28 g = 0.22 mol) were heated on a steam bath under reflux for 45 minutes. The solvent was removed in vacuo on a steam bath, the residue dissolved in 20 ml of water and the product precipitated by the gradual addition of 80 g of 25% sodium hydroxide solution at 0°C. A small additional amount was obtained by extraction of the mother liquor with methylene chloride. The product melted at 60°C. 

Chemical Name l-Methyl-2-(l-methylethyl)-5-nitro-lH-imidazole Common Name 2-Isopropyl-l-methyl-5-nitroimidazole Structural Formula ... 

SYNS IPRONIDAZOLE (USDA) 2-ISOPROPYL-l-METHYL-5-NITROIMIDAZOLE l-METHYL-2-(l-METHYLETHYL)-5-NITRO-lH-IMIDAZOLE RO 7-1554... 

More recently there has been some interest in the structures of the iV-nitration products of 4-nitroimidazoles. Both 4-nitro- (81UP40600) and 2-isopropyl-4-nitro-imidazole (72CJC3472) have been shown to iV-nitrate with such an orientation that the 1,4-dinitro compound results (see Figure 2). 

In a series of 1, 2-disubstituted 5-nitroimidazoles the most potent was 1-methyl-2-isopropyl-5 nitroimidazole which was 4 to 8 times more effective than others in the series and twice as active as dimetridazole in turkeys. Compound XIII is also reported to be active in histomoniasis in chickens. ... 

Methyl-4(5)-nitroimidazole added to a soln. of Na in methanol, evaporated to dryness, and the resulting Na-salt refluxed 2 hrs. in a mixture of isopropyl iodide and dimethylformamide -> 12 g. l-isopropyl-2-methyl-4-nitroimidazole. - The 5-nitro isomer was obtained by refluxing the above startg. m. with 2-propyl tosylate in benzene. M. Hoffer et al., J. Med. Chem. 14, 993 (1971). 

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