Synthesis
The general procedure for the synthesis of methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate from methanol and 2,2,2-trichloro-1-(1-methyl-4-nitro-1H-imidazol-2-yl)ethanone was as follows: methanol (40 mL) was added to a reaction flask containing 2,2,2-trichloro-1-(1-methyl-4-nitro-1H-imidazol-2-yl)ethanone, heated to 40 °C and stirred for 10 minutes. Subsequently, a small amount of sodium hydride (100 mg) was added to the reaction mixture to ensure complete methanolysis. After continued stirring for 2 h, the reaction mixture was filtered to afford methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate in 94% yield. The product was confirmed by 1H-NMR (CDCl3): δ 7.84 (s, 1H, Im-CH), 4.18 (s, 3H, CH3), 3.93 (s, 3H, CH3).EI-HRMS analysis resulted in a m/z calculated value of 185.0437 for C6H7N3O4 and a measured value of 185.0476 (100%).
References
[1] Patent: WO2007/45096, 2007, A1. Location in patent: Page/Page column 45; 86
[2] Heterocycles, 1995, vol. 41, # 6, p. 1181 - 1196
[3] Synthetic Communications, 2004, vol. 34, # 9, p. 1609 - 1615
