1-Methylimidazole → 1-methyl-3-[2-(2-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide

HRID 64655Notes

Reaction equation

HRID 64655 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=[O:4].[CH3:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(OCC)C>[Br-:1].[CH3:12][NH+:13]1[CH:17]=[CH:16][N:15]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:11])=[O:4])[CH2:14]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 124306762-Bromo-2'-methylacetophenone

Product 1

HCID 703877611-methyl-3-[2-(2-methylphenyl)-2-oxoethyl]-1H-imidazolium bromideYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.22 g (0.02 mol) of 1-bromo-2-(2-methylphenyl)-2-oxoethane, 2.64 g (0.032 mol) of 1-methylimidazole and 60 ml of diethyl ether was stirred at room temperature for approximately 17 hours. The reaction solvent was decanted and the residue was washed with diethyl ether. The residue was dissolved in hot acetonitrile, and the resulting solution was cooled and diluted with diethyl ether. The solid was collected and recrystallized twice from acetonitrile/diethyl ether to afford 1.99 g of 1-methyl-3-[2-(2-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide as white needles. (34% yield) mp=152°-154° C.

Workup

  1. customThe reaction solvent was decanted
  2. washthe residue was washed with diethyl ether
  3. dissolutionThe residue was dissolved in hot acetonitrile
  4. temperaturethe resulting solution was cooled
  5. additiondiluted with diethyl ether
  6. customThe solid was collected
  7. customrecrystallized twice from acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-6430354e504d454496bcc68817c2b954
Source dataset
uspto-grants-1986_09
Patent number
US04609670

Reaction notes

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