Reaction Steps
Imidazolium chloride [3] (312.8 mg, 1 mmol) and sodium docusate (444.6 mg, 1 mmol) were dissolved in 20 ml of acetone/H2O 1:1 and stirred overnight at room temperature. The remaining suspension was diluted with 50 ml of H2O and extracted with dichloromethane. The organic layer was washed successively with water until no more chloride ions could be detected in the washings (checked by addition of AgNO3 solution), dried over MgSO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to give imidazolium docusate [4] in quantitative yield as yellow oil. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=9.07 (s, 1H), 7.71 (s, 2H), 5.33 (t, J=7.3 Hz, 1H), 5.24 (s, 2H), 5.07 (m, 1H), 4.69 (d, J=7.3 Hz, 2H), 3.91 (s, 3H), 3.90 (m, 4H), 3.62 (dd, J1=11.39 Hz, J2=3.88 Hz, 1H), 2.86 (m, 2H), 2.04 (m, 4H), 1.68 (s, 3H), 1.65 (s, 3H), 1.57 (s, 3H), 1.49 (m, 2H), 1.24 (m, 16 H), 0.84 (m, 12H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=171.1, 168.1, 166.9, 142.7, 137.7, 131.2, 123.7, 123.6, 123.4, 117.6, 66.2, 66.1, 62.4, 61.4, 49.5, 38.1, 356.0, 34.1, 29.8, 29.6, 28.3, 25.8, 25.5, 23.2, 23.0, 22.4, 17.6, 16.2, 13.9, 10.8. T5%onset 170° C.
