1,2-Dimethylimidazole → HCID 86617157, compound

HRID 606556

Reaction equation

HRID 606556 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH3:18][N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH3:24]>CC#N>[Cl-:1].[CH3:18][N+:19]1[CH:23]=[CH:22][N:21]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:20]=1[CH3:24]

Participants

4

Reactant 2

HCID 156171,2-DimethylimidazoleHCID 209931-Chlorohexadecane

Product 1

HCID 86617157HCID 86617157, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer were added 1-chlorohexadecane (260 g, 1.00 moles), 1,2 dimethylimidazole (91.0 g, 0.95 moles), and CH3CN (500 mL) and the two-phase reaction mixture was vigorously stirred in an oil bath at 80° C. After 72 h, the reaction mixture was cooled to room temperature and the product was crystallized overnight. The crystallized solid was filtered, thoroughly washed with cold CH3CN, and vacuum dried at 70° C. for 3 days to give 1,2-dimethyl-3-hexadecylimidazolium chloride as a slightly off-white solid, 220 g, 62% yield.

Workup

  1. customTo a 2 L three-necked round bottom flask equipped with overhead mechanical stirrer
  2. customthe two-phase reaction mixture
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customthe product was crystallized overnight
  5. filtrationThe crystallized solid was filtered
  6. washthoroughly washed with cold CH3CN, and vacuum
  7. customdried at 70° C. for 3 days

Sources & evidence

ORD record
ord-a24e5dd4147d4b6e9c248ec7e7069ac6
Source dataset
uspto-grants-2011_03
Patent number
US07915332B2

Linked notes

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