methyl (3-nitro-1H-1,2,4-triazol-1-yl)acetate synthesis

Yield: 95.1%

Reaction Conditions:

Stage #1:3-nitro-1,2,4-triazole with potassium carbonate in acetonitrile at 50; for 0.5 h;Reflux;
Stage #2:methyl chloroacetate in acetonitrileReflux;

Steps:

4.1.2. Synthesis of methyl 2-(3-nitro- [1,2,4]triazol-1-yl)acetate (6)
11.41 g 5 (0.1 mol, 1 eq) and 15.29 g potassium carbonate(0.11 mol, 1.1 eq) was added to 100mL acetonitrile and stirred at50 °C for 0.5 h, the mixture turned to be bright yellow. 16.05 gmethyl bromoacetate (0.105 mol, 1.05 eq) was added to the mixtureand then reflux until no 5 appeared on TLC. The mixturewas cooledto room temperature and filtrated. The filtrate was evaporatedunder reduced pressure, and the residuewas dissolved in a mixtureof ethyl acetate and water. The organic layer was separated and theaqueous layer was extracted twice. The organic extracts werecombined, dried (anhydrous Na2SO4) and evaporated to dryness toafford 17.23 g 6 as brownish solid with the yield of 95.1%; ESI-MSm/z 187.04 [M H]; 1H NMR (400 MHz, DMSO-d6): d (ppm): 3.73(s, 3H), 5.43 (s, 2H), 8.86 (s, 1H)

References:

Wei, Huiqiang;Duan, Yuqing;Gou, Wenfeng;Cui, Jie;Ning, Hongxin;Li, Deguan;Qin, Yong;Liu, Qiang;Li, Yiliang [European Journal of Medicinal Chemistry,2019,vol. 181,art. no. 111552]