Fig nbsp shows the results

[GLY (mim)3][Br]3, Thick liquid: 1H NMR (400 MHz, DMSO-d6):∂ 3.51 (s, 3 × 3H), 3.83 (m, 5H), 8.80 (s, 3 × 1H), 7.71–7.80 (m, 3 × 2H). FT-IR (500–4000 cm− 1): 1198 cm− 1, 1210 cm− 1 (S = O), 1364 cm− 1, 1441 cm− 1 (C = C), 1623 cm− 1 (C = N), 3095 cm− 1(Ar–H), 2912 cm− 1, 2870 cm− 1(C–H). 13C NMR (125 MHz): 33.96, 39.58, 46.12, 50.25, 120.79, 128.55, 137.16. HR-MS m/z [M-OMs]+: 367.25. Analysis: C18H32Br3N6. Calcd (%): C 37.73, H 5.64, Br 41.89, N 14.69; Found: C 37.70, H 5.61, Br 41.91, N 14.65.
2.4. General procedure Gefitinib 2-azidoalcohol formation from epoxides
The procedure to synthesize 2-azidoalcohol was carried our using previously reported conditions [23]. In brief, epoxides (0.83 mol) and sodium azide (1.24 mol) was taken in a 50 ml round bottom flask. Then 0.15 mol of corresponding tri-cationic ILs/water (IL/H2O (2:1)) was used as catalyst/solvent in reaction media. The reaction mixture was heated at 60 °C for 60 to 180 min for different catalysts prepared in capsid study. Reaction progress was monitored by TLC using (5% ethyl acetate: hexane). After the completion of reaction, the obtained mixture was extracted three times with ether, dried in sodium sulfate (Na2SO4) and associated ether solvent was removed under reduced pressure. The resulting 2-azidoalcohol product was purified by column chromatography.