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

HRID 64659

Reaction equation

HRID 64659 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 hot 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 hot acetonitrile
  4. customrecrystallized twice from acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-5f078ae1843a466bba893ce12b967e2a
Source dataset
uspto-grants-1986_09
Patent number
US04609670

Linked notes

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