Potassium Carbonate → (1-But-3-en-1-yl-4-phenyl-1H-imidazol-2-yl)(3-methoxyphenyl)methanone

HRID 31545Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:46](Br)[CH2:47][CH:48]=[CH2:49]>CN(C=O)C.O>[CH2:49]([N:12]1[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=[C:11]1[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:10])[CH2:48][CH:47]=[CH2:46]

Participants

Conditions

Temperature: 80 °C

Procedure

(3-Methoxyphenyl)(4-phenyl-1H-imidazol-2-yl)methanone (278 mg, 1.00 mmol) was dissolved in DMF (3 ml), and thereto were added potassium carbonate (207 mg, 1.50 mmol), 18-crown-6 (26.4 mg, 0.100 mmol), 3-butenyl bromide (162 mg, 1.20 mmol), and the mixture was stirred at 80° C. for 5 hours. The reaction solution was cooled to room temperature, and thereto was added water. The mixture was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The resulting residue was subjected to azeotropic distillation with toluene to give the title compound (309 mg, 93%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionThe mixture was extracted with ethyl acetate
customthe solvent was evaporated under reduced pressure
distillationThe resulting residue was subjected to azeotropic distillation with toluene

Sources & evidence

ORD record: ord-7df9299ce8bc4106b99b50b43abefd25
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425642B2

Reaction notes

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