The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nucleophilic substitution reactions of 1-methyl-4,5-dinitroimidazole with aqueous ammonia or sodium azide》. Authors are Lian, Peng-Bao; Guo, Xiao-Jie; Wang, Jian-Long; Chen, Li-Zhen; Shen, Fan-Fan.The article about the compound:1-Methyl-4-nitro-1H-imidazol-5-aminecas:4531-54-8,SMILESS:NC1=C([N+]([O-])=O)N=CN1C).Name: 1-Methyl-4-nitro-1H-imidazol-5-amine. Through the article, more information about this compound (cas:4531-54-8) is conveyed.
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.
This compound(1-Methyl-4-nitro-1H-imidazol-5-amine)Name: 1-Methyl-4-nitro-1H-imidazol-5-amine was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.
Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem