Potassium Carbonate → Ethyl 4-(2-methyl-1H-imidazol-1-yl)benzoate

HRID 1108062Notes

Reaction equation

HRID 1108062 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.F[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][C:2]1[N:3]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 14664350Ethyl 4-(2-methyl-1H-imidazol-1-yl)benzoateYield 34%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-methylimidazole (50 g, 0.6 mol), ethyl 4-fluorobenzoate (100 g, 0.6 mol) and potassium carbonate (415 g, 3 mol) in dry DMSO (1.5 l ) was heated at 120° C. for 66 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into ice-cold water (1 l ), and extracted with Et2O (750 ml×2). The organic phase was washed with water (500 ml) and brine (500 ml), dried over MgSO4 and evaporated. The residual solid was recrystallized from ethyl acetate-hexane to give the titled compound (47 g, 33%) as yellow needles.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with Et2O (750 ml×2)
  3. washThe organic phase was washed with water (500 ml) and brine (500 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residual solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5d42b403e81540ffb98a27144559e735
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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