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

HRID 2119223Notes

Reaction equation

HRID 2119223 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)=[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]=[C:7]([CH3:11])[CH:6]=2)=[O:4])[CH2:14]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 100361292-Bromo-1-(3-methylphenyl)ethan-1-one

Product 1

HCID 703875941-methyl-3-[2-(3-methylphenyl)-2-oxoethyl]-1H-imidazolium bromideYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5.16 g (0.024 mol) of 1-bromo-2-(3-methylphenyl)-2-oxoethane and 2.15 g (0.026 mol) of 1-methylimidazole in approximately 30 ml of diethyl ether was stirred at room temperature for about 19 hours. The reaction solvent was decanted and the resulting brown residue was washed with diethyl ether. The residue was washed with not acetonitrile and recrystallized twice from acetonitrile/diethyl ether to afford 1.74 g of 1-methyl-3-[2-(3-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide as white needles. (25% yield) mp=185°-187° C.

Workup

  1. customThe reaction solvent was decanted
  2. washthe resulting brown residue was washed with diethyl ether
  3. washThe residue was washed with not acetonitrile
  4. customrecrystallized twice from acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-e67f0a9cd29b46399bdb475cbee53a89
Source dataset
uspto-grants-1987_07
Patent number
US04683312

Reaction notes

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