1-Methylimidazole → 1-methyl-3-(1,1-dimethyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromide

HRID 64653Notes

Reaction equation

HRID 64653 reaction equation
[Br:1][C:2]([CH3:12])([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>C(OCC)C>[Br-:1].[CH3:13][NH+:14]1[CH:18]=[CH:17][N:16]([C:2]([CH3:12])([CH3:11])[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH2:15]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 66324Phenyl 2-bromo-2-propyl ketone

Product 1

HCID 703875781-methyl-3-(1,1-dimethyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromideYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.6 g (0.02 mol) of α-bromoisobutyrophenone and 1.8 g (0.022 mol) of 1-methylimidazole in 30 ml of diethyl ether was stirred at room temperature for approximately 48 hours. The solvent was decanted and the resulting oil was slurried in ethyl acetate. The solvent was again decanted and the residue was dissolved in acetonitrile prior to adding a small portion of ethyl acetate. A white precipitate was collected by filtration and recrystallized from methanol/ethyl acetate to afford 3.88 g of 1-methyl-3-(1,1-dimethyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromide as glittering white flakes. (63% yield) mp=137°-140° C.

Workup

  1. customThe solvent was decanted
  2. customThe solvent was again decanted
  3. dissolutionthe residue was dissolved in acetonitrile
  4. additionto adding a small portion of ethyl acetate
  5. filtrationA white precipitate was collected by filtration
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-8104772c20514b93bc2857cc39bb66e2
Source dataset
uspto-grants-1986_09
Patent number
US04609670

Reaction notes

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