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

HRID 2119220Notes

Reaction equation

HRID 2119220 reaction equation
[C:1]1([C:7](=[O:11])[CH:8]([Br:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(OCC)C>[Br-:10].[CH3:12][NH+:13]1[CH:17]=[CH:16][N:15]([CH:8]([CH3:9])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:11])[CH2:14]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 164522-Bromopropiophenone

Product 1

HCID 703877441-methyl-3-(1-methyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromideYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 8 ml (0.047 mol) of 90% pure 1-phenyl-1-oxo-2-bromopropane and 4.25 g (0.052 mol) of 1-methylimidazole in 100 ml of diethyl ether was stirred at room temperature for approximately 24 hours. The precipitated solid was collected by filtration, washed with diethyl ether and dissolved in methanol. This solution was diluted with diethyl ether and the resulting white solid was collected by filtration. This solid was recrystallized from methanol/diethyl ether to afford 7.65 g of 1-methyl-3-(1-methyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromide as white crystals. (55% yield) mp=167°-170° C.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with diethyl ether
  3. dissolutiondissolved in methanol
  4. additionThis solution was diluted with diethyl ether
  5. filtrationthe resulting white solid was collected by filtration
  6. customThis solid was recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-a2ab89aa4f8141dea0296134b6759bd4
Source dataset
uspto-grants-1987_07
Patent number
US04683312

Reaction notes

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