Hydrochloric Acid → 1-(4-Nitrophenyl)-1H-imidazole

HRID 2236725Notes

Reaction equation

HRID 2236725 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 9590p-FluoronitrobenzeneHCID 10340Sodium Carbonate

Product 1

HCID 1231551-(4-Nitrophenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a 20 mL vial were combined 4-fluoronitrobenzene (1.1 mL, 10 mmol), imidazole (0.68 g, 10 mmol), and sodium carbonate (1.1 g, 11 mmol) in N,N-dimethylformamide (5 mL). The mixture is shaken at 100° C. for 24 hours and then allowed to cool to room temperature and then diluted with water. Concentrated hydrochloric acid is added to bring the pH to 1, and then the mixture is extracted thrice with chloroform (10 mL). The acidic aqueous phase is then treated with 2.5 M sodium hydroxide solution to give a pH of 10. A light yellow solid is collected and washed with water to give 1-(4-nitrophenyl)-1H-imidazole.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture is extracted thrice with chloroform (10 mL)
  3. additionThe acidic aqueous phase is then treated with 2.5 M sodium hydroxide solution
  4. customto give a pH of 10
  5. customA light yellow solid is collected
  6. washwashed with water

Sources & evidence

ORD record
ord-0d3b9626b96048789e06de29e548b685
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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