1-Methylimidazole → HCID 178460460, compound

Participants

Reaction Steps

This intermediate is then quaternarized with 3-methylimidazole. Under N2 atmosphere, a mixture of 11-bromoundecylacrylate (6.08 g, 20 mmol) and 1-methylimidazole (1.64 g, 20 mmol) and a small amount of 2,6-di-tert-butyl-4-methylphenol (inhibitor) was stirred at 40° C. for 48 h, and yielded a viscous liquid. The viscous liquid was purified by the precipitation method with diethyl ether to obtain yellow viscous liquid 1-(2-acryloyloxyundecyl)-3-methylimidazolium bromide. The viscous liquid was dried under vacuum at room temperature as the white waxy solid (5.73 g, 74%). 1H NMR (400 MHz, CDCl3): 10.66 (1H, m, N—CH—N), 7.34-7.25 (2H, s, N—CH═CH—N), 6.36-6.35 (1H, m, CH2═CH), 6.14-6.11 (1H, m, CH2═CH), 5.81-5.79 (1H, m, CH2═CH), 4.30-4.29 (2H, t, N—CH2(CH2)10O—), 4.11 (3H, s, N—CH3), 1.90-1.82 (2H, t, N—CH2(CH2)10O—), 1.66-1.62 (2H, m, —OCOCH2CH2), 1.30-1.24 (14H, m, —CH2CH2(CH2)7CH2CH2—). Elemental analysis: Calculated: C18H32BrN2O2, C, 55.67%; H, 8.31%; N, 7.21%. Found: C, 55.22%, H, 7.79%, N, 7.35%. mp: 37.2° C.

Provenance & Evidence