Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Chemistry of Heterocyclic Compounds (New York, NY, United States) called Nucleophilic substitution reactions of 1-methyl-4,5-dinitroimidazole with aqueous ammonia or sodium azide, Author is Lian, Peng-Bao; Guo, Xiao-Jie; Wang, Jian-Long; Chen, Li-Zhen; Shen, Fan-Fan, which mentions a compound: 4897-25-0, SMILESS is C1=NC(=C(Cl)[N]1C)[N+]([O-])=O, Molecular C4H4ClN3O2, Synthetic Route of C4H4ClN3O2.
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, m.ps., and elemental anal. 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 occurred in aqueous ammonia. Only one nitro group of the two is involved in nucleophilic substitution reaction in each case.
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Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts