Imidazole → 1-[3-(4-Ethoxycarbonylphenoxy)propyl]imidazole

HRID 745927Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (0.6 g, 50% suspension in mineral oil) was added cautiously to a stirred and cooled solution of imidazole (0.79 g) in dry N,N-dimethylformamide (50 ml). After the initial vigorous reaction had subsided the mixture was heated to 100° C. for 10 minutes and then stirred at room temperature for a further 1 hour. Ethyl 4-(3-chloropropoxy)benzoate (2.8 g) was added over 2 minutes and the resulting mixture was heated on a steam bath for 6 hours and then cooled. Water (1 ml) was added to decompose any unreacted sodium hydride and the solution was evaporated and the residue was chromatographed on silica gel. Elution with chloroform gave mineral oil and small amounts of impurity. Elution with chloroform/methanol (20:1) gave the pure 1-[3-(4-ethoxycarbonylphenoxy)propyl]imidazole as an oil on evaporation of the solvent.

Workup

customAfter the initial vigorous reaction
stirringstirred at room temperature for a further 1 hour
temperaturethe resulting mixture was heated on a steam bath for 6 hours
temperaturecooled
customthe solution was evaporated
customthe residue was chromatographed on silica gel
washElution with chloroform
customgave mineral oil and small amounts of impurity
washElution with chloroform/methanol (20:1)

Sources & evidence

ORD record: ord-5e11406b07c84e408a86c268d4ce1322
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04602016

Reaction notes

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