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

HRID 1668274Notes

Reaction equation

HRID 1668274 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.F[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:14][O:13][C:11]([C:10]1[CH:15]=[CH:16][C:7]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:8][CH:9]=1)=[O:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoate

Product 1

HCID 2766374Methyl 4-(1H-imidazol-1-yl)benzoateYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of imidazole (132 g, 1.9 mol), methyl 4-fluorobenzoate (170 ml, 1.3 mol) and potassium carbonate (357 g, 2.6 mol) in DMSO (200 ml) is stirred at 120° C. for 3 h. After cooling to room temperature, the mixture is added to ice-water. Precipitated product is filtered off and washed with water. Yield: 59%.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationPrecipitated product is filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-0cef180ce2cc4b3cbe4fcec96a5d2fd5
Source dataset
uspto-grants-2011_08
Patent number
US07989091B2

Reaction notes

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