Imidazole → Ethyl 4-(1H-imidazol-1-yl)benzoate

HRID 355738

Reaction equation

HRID 355738 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.F[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 13423940Ethyl 4-(1H-imidazol-1-yl)benzoateYield 56.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Imidazole (0.816 g, 0.01 mol), ethyl 4-fluorobenzoate (2 g, 0.01 mol) and anhydrous potassium carbonate (1.43 g, 0.011 mol) was dissolved in DMSO (30 ml) and heated to 90° C. for 18 h. The solution was poured into water (50 ml), extracted with ethyl acetate (50 ml), dried (sodium sulphate), filtered and evaporated to dryness under reduced pressure. The white solid was purified by flash column chromatography (silica, diethyl ether) to afford a white solid (1.22 g, 56%).

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. dry with materialdried (sodium sulphate)
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe white solid was purified by flash column chromatography (silica, diethyl ether)

Sources & evidence

ORD record
ord-a3d33c33f5864abeb2dabc05dc915596
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Linked notes

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