4875-33-6Relevant academic research and scientific papers
Nucleophilic substitution reactions of 1-methyl-4,5-dinitroimidazole with aqueous ammonia or sodium azide
Lian, Peng-Bao,Guo, Xiao-Jie,Wang, Jian-Long,Chen, Li-Zhen,Shen, Fan-Fan
, p. 1045 - 1049 (2018)
[Figure not available: see fulltext.] In this work, 5-amino-1-methyl-4-nitroimidazole was synthesized by amination reaction of 1-methyl-4,5-dinitroimidazole with aqueous ammonia in 95% yield. Meanwhile, one of its isomers, 4-amino-1-methyl-5-nitroimidazole as byproduct was obtained from the filtrate. Furthermore, nucleophilic substitution reaction of 1-methyl-4,5-dinitroimidazole with sodium azide gave 5-azido-1-methyl-4-nitroimidazole in 98% yield. The three compounds were characterized by IR, 1H and 13C NMR spectra, melting points, and elemental analysis. The structure of 4-amino-1-methyl-5-nitroimidazole was further confirmed by single crystal X-ray diffraction. These reactions indicate that the nitro group at position 5 of 1-methyl-4,5-dinitroimidazole is quite unstable, as well as partial substitution of nitro group at position 4 also occured in aqueous ammonia. Only one nitro group of the two is involved in nucleophilic substitution reaction in each case.
