p-Fluoronitrobenzene → ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylate

HRID 2366880Notes

Reaction equation

HRID 2366880 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:2]1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:1]2[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:2]2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178469898HCID 178469898, compound

Product 1

HCID 18726773ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylateYield 84.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 1H-imidazole-4-carboxylate (8 g, 57.1 mmol), 4-fluoro-1-nitrobenzene (8.05 g, 57.1 mmol) and potassium carbonate (8.68 g, 62.8 mmol) in acetonitrile (100 mL) was stirred at 60° C. for 16 h then cooled to room temperature and most the solvent was removed in vacuo. The residue was partitioned between AcOEt (200 mL) and water (150 mL) and the layers were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM) gave ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylate (12.53 g, 48.0 mmol, 84%) as a yellow oil.

Workup

  1. temperaturethen cooled to room temperature
  2. custommost the solvent was removed in vacuo
  3. customThe residue was partitioned between AcOEt (200 mL) and water (150 mL)
  4. customthe layers were separated
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-8a8af0830f3d4e42be10cc3378a45794
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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