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

HRID 1462925Notes

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]

Participants

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

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