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

HRID 2119216Notes

Reaction equation

HRID 2119216 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH3:13])[CH:6]=1)=[O:4].[CH3:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>C(#N)C.CO>[Br-:1].[CH3:14][NH+:15]1[CH:19]=[CH:18][N:17]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH3:13])[CH:6]=2)=[O:4])[CH2:16]1

Participants

5

Reactant 2

HCID 13901-MethylimidazoleHCID 226410062-Bromo-1-(3-ethoxyphenyl)ethanone

Product 1

HCID 703876021-methyl-3-[2-(3-ethoxyphenyl)-2-oxoethyl]-1H-imidazolium bromideYield 7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.9 g (0.012 mol) of 1-bromo-2-(3-ethoxyphenyl)-2-oxoethane in 20 ml of acetonitrile was combined with 1.03 g (0.013 mol) of 1-methylimidazole and the resulting mixture was stirred at room temperature for approximately 18 hours. The mixture was diluted with methanol and the volatiles were evaporated under reduced pressure to a volume of approximately 15 ml. This solution was diluted with ethyl acetate and the precipitated brown solid was collected by filtration. The collected solid was washed with ethyl acetate and dissolved in hot acetonitrile. The mixture was purified with charcoal and upon cooling the solid was collected. The solid was recrystallized from acetonitrile/diethyl ether to provide two crops which were combined and recrystallized three times from isopropyl alcohol to afford 0.27 g of 1-methyl-3-[2-(3-ethoxyphenyl)-2-oxoethyl]-1H-imidazolium bromide as pale yellow flakes. (7% yield) mp=137°-138° C.

Workup

  1. customthe volatiles were evaporated under reduced pressure to a volume of approximately 15 ml
  2. additionThis solution was diluted with ethyl acetate
  3. filtrationthe precipitated brown solid was collected by filtration
  4. washThe collected solid was washed with ethyl acetate
  5. dissolutiondissolved in hot acetonitrile
  6. customThe mixture was purified with charcoal
  7. temperatureupon cooling the solid
  8. customwas collected
  9. customThe solid was recrystallized from acetonitrile/diethyl ether
  10. customto provide two crops which
  11. customrecrystallized three times from isopropyl alcohol

Sources & evidence

ORD record
ord-4a95767e58cc430790434b00f021eb6b
Source dataset
uspto-grants-1987_07
Patent number
US04683312

Reaction notes

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