So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Lian, Peng-Bao; Guo, Xiao-Jie; Wang, Jian-Long; Chen, Li-Zhen; Shen, Fan-Fan researched the compound: 1-Methyl-4-nitro-1H-imidazol-5-amine( cas:4531-54-8 ).Related Products of 4531-54-8.They published the article 《Nucleophilic substitution reactions of 1-methyl-4,5-dinitroimidazole with aqueous ammonia or sodium azide》 about this compound( cas:4531-54-8 ) in Chemistry of Heterocyclic Compounds (New York, NY, United States). Keywords: nucleophilic substitution reaction methyldinitroimidazole aqueous ammonia sodium azide. We’ll tell you more about this compound (cas:4531-54-8).
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:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem