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1-(1H-Imidazol-1-yl)ethanone → 1-Acetyl-3-[4-(ethoxycarbonylmethoxy)benzyl]imidazolium bromide

HRID 1462925
Notes
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Reaction equation

HRID 1462925 reaction equation
[C:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)(=[O:3])[CH3:2].[Br:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1>C(#N)C>[Br-:9].[C:1]([N+:4]1[CH:8]=[CH:7][N:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][CH:23]=2)[CH:5]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 12870369Ethyl 2-[4-(bromomethyl)phenoxy]acetate

Product 1

HCID 1784729941-Acetyl-3-[4-(ethoxycarbonylmethoxy)benzyl]imidazolium bromideYield 98.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2.2 g of 1-acetylimidazole and 5.46 g of ethyl 4-bromomethylphenoxyacetate were added to 5 ml of dry acetonitrile, and the mixture was heated at 60° C. for 2 hours. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was triturated with an adequate amount of dry diethyl ether and the resulting powder was collected by filtration and dried to obtain 7.5 g of 1-acetyl-3-[4-(ethoxycarbonylmethoxy)benzyl]imidazolium bromide. (98.6% yield). Colorless hygroscopic amorphous.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was triturated with an adequate amount of dry diethyl ether
  4. filtrationthe resulting powder was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-9f7b7a89136c4505bf9652555cd7e002
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04461905

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes