1-氨基-3-十二烷基-1,2,3-三唑硝酸盐的合成研究

Synthesis of 1-Amino-3-Dodecyl-1,2,3-Triazolium Nitrate

以乙二醛、水合肼及溴代十二烷为原料,经加成—消除、环化、烷基化、复分解4步反应得到1-氨基-3-十二烷基-1,2,3-三唑硝酸盐。通过核磁、红外、质谱等分析手段对目标产物进行了结构表征。探索并优化了加成—消除、环化和烷基化反应条件。各步反应的最佳条件为:加成—消除反应中,n(水合肼)n(乙二醛)n(甲醇)=319,70℃反应5 h,收率为90.3%;环化反应中,m(二氧化锰)m(乙二腙)=21,20℃反应3h,收率为88.2%;烷基化反应中,n(1-氨基-1,2,3-三唑)n(溴代十二烷)=11.5,80℃反应40h,收率为64.5%;复分解反应易进行且得率高,反应3.5h,产率为80.4%,目标产物总收率为41.3%。

Amino-3-dodecyl-1, 2, 3-triazolium nitrate was synthesized through 4 steps including addition-elimina- tion, cyclization, alkylation and double replacement reaction by using glyoxal, hydrazine and bromododecane. The products were characterized by NMR, FT-IR and MS. The reaction conditions of addition-elimination, cyclization and alkylation were explored and optimized. The optimal conditions for each step of the reactions are as follows： In addition-elimination reaction, n（ hydrazine hydrate） ： n（glyoxal） ： n（methanol） = 3 ： 1 ： 9, 70% for 5 h with a yield of 90.3% ; In cycliza- tion reaction, m（ MnOz ） ： m（ glynxal bishydrazone） = 2 ： 1, 20℃ for 3 h with a yield of 88.2% ; In alkylation reaction, n（1-amino-I ,2,3-triazole） ： n（bromododecane） = 1 ： 1.5, 80℃ for 40 h with a yield of 64.5%. The fourth step is a simple metathesis reaction with a high yield, in which the reaction time is 3.5h and the yield is 80.4%. The total yield of target product is 41.3%.