Nitrophenyl nitroimidazole

The selective hydrogenation of the nitrophenyl-nitroimidazole, 8, was accomplished in 85-90% yield by careful attention to reaction conditions.29 The maximum yield of 9 (Eqn. 19.13) was obtained using a Pd/C catalyst with concentrated aqueous ammonia as the solvent at 20-35°C and 2.7 atmospheres. Variation from these conditions resulted in a significant decrease in selectivity. The need for these exacting conditions arose because of two critical requirements (1) the imidazole ring should exist as its anion to inhibit the hydrogenation of the imidazole nitro group and (2) the concentration of reactant in solution should be... 

Methyl-4-nitro-l-(4-nitrophenyl)imidazole (nitrefazole, altimol) 4-Nitro- 1-carboxymethylimidazole Methyl-4-nitromidazole-5-carboxylate l,2-Dimethyl-4-nitroimidazole, 8609 RP... 

Related reactions include the formation of the 2-cyano compounds (190) when 1,2-dimethyl-5-nitroimidazole is heated with nitrosyl chloride or an AT-oxide, and when 2-methyl-l-(o-nitrophenyl)imidazoles (191) cyclize under the influence of iron(II) oxalate (Scheme 98) (74JCS(P1)1970). The last reaction product is contaminated by a large amount of amine reduction product ( 64%) but there is also some cyclization with the 4-methyl isomer of (191). In the presence of trimethylamine, 2-cyanomethylbenzimidazole condenses with acetone to give the unsaturated derivative (192 Scheme 99) (77CPB3087). Neither 2-methylimidazole nor 2-methylbenzimidazole reacts with formamide in the presence of phosphoryl chloride. 

Dimethyl-2-neopentyl-1-pentene. See 2-(2,2-Dimethylpropyl)-4,4-dimethylpent-1-ene 1,2-Dimethyl-5-nitroimidazole 1,2-Dimethyl-5-nitro-IH-imidazole. See Dimetridazole Dimethyinitromethane. See 2-Nitropropane 0,0-Dimethyl-0-(4-nitro-3-methylphenyl) thiophosphate. See Fenitrothion Dimethyl p-nitrophenyl monothiophosphate 0,0-Dimethyl-0-4-nitrophenyl phosphorothioate 0,0-Dimethyl 0-p-nitrophenyl phosphorothioate Dimethyl 4-nitrophenyl phosphorothionate Dimethyl-p-nitrophenyl thionphosphate. See Parathion-methyl... 

Where, R = Nitrofuran, nitrothiophene, nitrophenyl, N-methyl-nitroimidazole. 

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