Imidazole → Ethyl p-(1-imidazolyl)acetylaminobenzoate

HRID 1249545Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][C:10]([NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1)=[O:11]>CN(C)C=O>[N:3]1([CH2:9][C:10]([NH:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)=[O:11])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2.4 g of 50% sodium hydride in 100 ml of dry dimethylformamide was added slowly 3.4 g of imidazole at room temperature, and the mixture was heated to 80° C. A solution of 12.1 g of ethyl p-chloroacetylaminobenzoate in 45 ml of dry dimethylformamide was added to the mixture over a period of 30 minutes at 80° C., and then the reaction mixture was heated at 100° C. for 1.5 hours. After removal of the solvent under reduced pressure, the residue was dissolved in chloroform and washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residual solid was recrystallized from ethanol-n-hexane to give 10.5 g of ethyl p-(1-imidazolyl)acetylaminobenzoate as colorless needles. M.P.: 185°-187° C.

Workup

temperaturethe reaction mixture was heated at 100° C. for 1.5 hours
customAfter removal of the solvent under reduced pressure
dissolutionthe residue was dissolved in chloroform
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residual solid was recrystallized from ethanol-n-hexane

Sources & evidence

ORD record: ord-021e87cfb686432f98787d2382cc3edb
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04632934

Reaction notes

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