1-Methylimidazole → HCID 178442865, compound

HRID 1510591Notes

Reaction equation

HRID 1510591 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(#N)C>[Br-:7].[CH2:8]([N+:4]1[CH:5]=[CH:6][N:2]([CH3:1])[CH:3]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 813551-Bromodocosane

Product 1

HCID 178442865HCID 178442865, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

About 2 g (0.025 mol) of 1-methylimidazole and 10.7 g (0.026 mol) of 1-bromodocosane were dissolved into 20 mL of acetonitrile. The mixture was refluxed at 85° C. for 24 hours, and subsequently cooled down to room temperature. The resulting samples (cake like) were filtered and washed with ethyl ether three times. The final product: 1-docosanyl-3-methylimidazolium bromide was obtained as a white powder after being dried in a vacuum oven. The yield of this procedure was 81.4% with a melting point (Mp): 82.9° C. The spectra of 1H NMR (CDCl3 as the solvent, δ, ppm) were: 10.713 (N—CH—N, s, 1H), 7.274 (N—CH—CH, s, 1H), 7.218 (N—CH—CH, s, 1H), 4.310 (N—CH2, t, 2H), 4.130 (N—CH3, s, 3H), 1.918 (N—CH2—CH2, m, 2H), 1.248 (N—CH2—CH2—(CH2)19, m, 38H), 0.874 (CH3, t, 3H).

Workup

  1. temperaturesubsequently cooled down to room temperature
  2. filtrationThe resulting samples (cake like) were filtered
  3. washwashed with ethyl ether three times

Sources & evidence

ORD record
ord-7ee8f47b60434d4b98f771d871c30fe4
Source dataset
uspto-grants-2012_07
Patent number
US08211958B2

Reaction notes

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