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

HRID 842697Notes

Reaction equation

HRID 842697 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)=[O:5])[CH3:2].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-].[Na+].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10340Sodium CarbonateHCID 178469898HCID 178469898, compound

Product 1

HCID 18726773ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1H-imidazole-4-carboxylic acid ethyl ester (J.Het.Chem., 19, 253 (1982)) (584 mg, 4.17 mmol), 4-fluoronitrobenzene (588 mg, 4.17 mmol) and anhydrous sodium carbonate (487 mg, 4.59 mmol) in dry dimethylformamide (10 ml) was heated at 50° C. for 24 hours under nitrogen. After cooling to room temperature the mixture was poured into ice-cold water (60 ml) and the resulting solid collection by filtration, washed with water and dried under reduced pressure at 60° C. to give 1-(4-nitrophenyl)imidazole-4-carboxylic acid ethyl ester (980 mg, 90%) as an off-white solid, m.p. 198-200° C.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customthe resulting solid collection
  3. filtrationby filtration
  4. washwashed with water
  5. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-3140875dfeb1451eb40442a3fe705ae3
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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