1-Methylimidazole → HCID 178460460, compound

HRID 2357020Notes

Reaction equation

HRID 2357020 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Br:7]C[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20](=[O:23])[CH:21]=[CH2:22].[C:24](C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>>[Br-:7].[C:20]([O:19][CH:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])[CH2:1][N+:2]1[CH:6]=[CH:5][N:4]([CH3:24])[CH:3]=1)(=[O:23])[CH:21]=[CH2:22]

Participants

4

Reactant 3

HCID 13901-Methylimidazole2×HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 1384139611-Bromoundecyl prop-2-enoate

Product 1

HCID 178460460HCID 178460460, compound

Procedure

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.

Workup

  1. customyielded a viscous liquid
  2. customThe viscous liquid was purified by the precipitation method with diethyl ether

Sources & evidence

ORD record
ord-d5d15025e7214eac803480c15c3704b8
Source dataset
uspto-grants-2010_07
Patent number
US07759401B2

Reaction notes

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