《Preparation of 1-methyl-2,4,5-trinitroimidazole from derivatives of 1-methylimidazole and its oxidation under nitration conditions》 was written by Lian, Peng-Bao; Chen, Jian; Chen, Li-Zhen; Zhao, Chong-Yang; Wang, Jian-Long; Shen, Fen-Fen. Synthetic Route of C4H6N2 And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2020. The article conveys some information:
1-Methylimidazole, 1-methyl-4-nitroimidazole, 1-methyl-5-nitroimidazole, or 1-methyl-4,5-dinitroimidazole gave a mixture of 1-methyl-4,5-dinitroimidazole and 1-methyl-2,4,5-trinitroimidazole under the volume ratio of HNO3 to H2SO4 of 1:3 at 80° temperature for 2.5 h, and the highest unisolated yield of 1-methyl-2,4,5-trinitroimidazole was 2.4%. 1-Methyl-2,4,5-trinitroimidazole was prepared from 1-methyl-2-nitroimidazole, 1-methyl-2,4-dinitroimidazole, or 1-methyl-2,5-dinitroimidazole under the same conditions, and the yields were 65, 76, and 82%, resp. However, when the ratio of HNO3 to H2SO4 was 1:5 and reaction was carried out at 120° for 2.5 h, only 1-methyl-4,5-dinitroimidazole was obtained from 1-methylimidazole, 1-methyl-4-nitroimidazole, or 1-methyl- 5-nitroimidazole in yields 43, 64, and 81%, resp. 1-Methyl-2-nitroimidazole, 1-methyl-2,4-dinitroimidazole, or 1-methyl- 2,5-dinitroimidazole gave 1-methylimidazolidine-2,4,5-trione under the same conditions, the yields were 61, 63, and 65%, resp. Meanwhile, 1-methylimidazolidine-2,4,5-trione was obtained from 1-methyl-2,4,5-trinitroimidazole. Under strong nitration conditions, the nitro group at the C-2 position is a key substituent to promote oxidation of the imidazole ring. The possible reaction mechanism for the formation of 1-methylimidazolidine-2,4,5-trione from 1-methyl-2,4,5-trinitroimidazole is given. The structure of 1-methylimidazolidine-2,4,5-trione was further confirmed by single crystal X-ray diffraction. In the experimental materials used by the author, we found 1-Methyl-1H-imidazole(cas: 616-47-7Synthetic Route of C4H6N2)
1-Methyl-1H-imidazole(cas: 616-47-7) is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate.Synthetic Route of C4H6N2
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem