1-Methylimidazole → 1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide

HRID 64651

Reaction equation

HRID 64651 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][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][C:8]([CH3:11])=[CH:7][CH:6]=2)=[O:4])[CH2:14]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 703875851-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromideYield 32.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10.6 g (0.05 mol) of 1-bromo-2-(4-methylphenyl)-2-oxoethane in 150 ml of diethyl ether was added 4.18 g (0.051 mol) of 1-methylimidazole (Aldrich Chemical Company, Milwaukee, Wis.). The reaction mixture was stirred for approximately 3 hours at room temperature and the precipitated solid was collected by filtration. The resulting hygroscopic solid was recrystallized from methanol/ethyl acetate to afford 4.82 g of 1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide as a solid. A second crop was obtained from the filtrate to provide an additional 5.8 g of product. (72% yield) mp=148°-151° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe resulting hygroscopic solid was recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-8f4205b623cb435d9102b80b41fd184e
Source dataset
uspto-grants-1986_09
Patent number
US04609670

Linked notes

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