NUCLEOPHILIC SUBSTITUTION REACTIONS OF 1-METHYL-4,5-DINITROIMIDAZOLE WITH AQUEOUS AMMONIA OR SODIUM AZIDE

Авторы

  • Peng-Bao Lian School of Chemical Engineering and Technology, North University of China, College road on the 3rd, Taiyuan 030051
  • Xiao-Jie Guo Shanxi DaYi Hospital (Shanxi Academy of Medical Sciences), 186 Long cheng St., Taiyuan 030032
  • Jian-Long Wang School of Chemical Engineering and Technology, North University of China, College road on the 3rd, Taiyuan 030051
  • Li-Zhen Chen School of Chemical Engineering and Technology, North University of China, College road on the 3rd
  • Fan-Fan Shen School of Chemical Engineering and Technology, North University of China, College road on the 3rd, Taiyuan 030051

DOI:

https://doi.org/10.1007/4665

Ключевые слова:

4-amino-1-methyl-5-nitroimidazole, 5-amino-1-methyl-4-nitroimidazole, 5-azido-1-methyl-4-nitroimidazole, 1-methyl- 4, 5-dinitroimidazole, nucleophilic substitution reaction

Аннотация

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.

Опубликован

2018-12-12

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Оригинальные статьи