Research on a New Synthesis of LLM-105 Using N-Nitroso-bis(cyanomethyl)amine

A new three-step synthetic method was designed to prepare 2,6-diamino- 3,5-dinitropyrazine 1-oxide (LLM-105) with an overall yield of 43.5%, using iminodiacetonitrile, triethylamine and hydroxylamine hydrochloride as the starting materials, and involved nitrosylation, cyclization and nitration. The structure of LLM-105 was characterized by FTIR, 1H NMR spectroscopy and elemental analysis. The crucial factors and mechanism of the cyclization were explored. Thermal decomposition, mechanical sensitivity and the purity of the LLM-105 were determined by TG-DTA, an impact sensitivity instrument and high performance liquid chromatography (HPLC) respectively. The results showed that LLM-105 synthesised via 2,6-diamino-3,5-dinitropyrazine (ANPZ) was less sensitive to impact, but the LLM-105 synthesized by the new method had some obvious advantages in terms of purity, security and production costs. Moreover, the LLM-105 synthesized by this new method can be initiated reliably without recrystallization.