1-Methylimidazole → HCID 178443225, compound

HRID 2357019Notes

Reaction equation

HRID 2357019 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>>[Br-:1].[CH2:2]([N+:17]1[CH:18]=[CH:19][N:15]([CH3:14])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 13901-MethylimidazoleHCID 89191-Bromododecane

Product 1

HCID 178443225HCID 178443225, compoundYield 94.4%

Conditions

Temperature
75 °C

Procedure

A mixture of 1-bromododecane (12.4 g, 50 mmol) and 1-methylimidazole (4.1 μg, 50 mmol) was stirred at 75° C. for 24 h. The viscous liquid was washed with ethyl acetate several times and heated at 85° C. under vacuum for 24 h to produce waxy 1-dodecyl-3-methylimidazolium bromide (15.64 g, 83%). 1H NMR (400 MHz, CDCl3): 10.61 (1H, m, N—CH—N), 7.25-7.34 (2H, s, N—CH═CH—N), 4.32-4.30 (2H, t, N—CH2(CH2)10CH3), 4.12 (3H, s, N—CH3), 1.91-1.90 (2H, m, N—CH2(CH2)10CH3), 1.32-1.23 (18H, m, N—CH2(CH2)10CH3), 0.87-0.84 (3H, t, N—CH2(CH2)10CH3). Elemental analysis: Calculated C16H32BrN2: C, 57.28%, H, 9.71%, N, 8.43%; Found: C, 56.62%, H, 9.49%, N, 8.35%. mp: 39.7° C.

Workup

  1. washThe viscous liquid was washed with ethyl acetate several times
  2. temperatureheated at 85° C. under vacuum for 24 h

Sources & evidence

ORD record
ord-2eb71bcec7bb41a98791f254da7e4b5e
Source dataset
uspto-grants-2010_07
Patent number
US07759401B2

Reaction notes

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