p-Fluoronitrobenzene → HCID 57154890, compound

HRID 610138Notes

Reaction equation

HRID 610138 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:19]2[C:18]([CH3:17])=[CH:22][N:21]=[CH:20]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178418800HCID 178418800, compound

Product 1

HCID 57154890HCID 57154890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of p-nitrofluorobenzene (2 g, 14 mmol) in DMF (20 mL) was treated with potassium carbonate (8 g, 58 mmol) and 4-methylimidazole (1.2 g, 14 mmol). After refluxing for 18 h, the reaction mixture was cooled down and concentrated at reduced pressure. The residue was treated with water and the mixture was extracted with ethyl acetate and dried over magnesium sulphate. The organic layer was concentrated and the residue was purified by flash-chromatography (methanol/methylene chloride, 0.5:9.5) affording 1.8 g (62%) of p-nitro-4 (5)-methyl-imidazol-1-yl as 7:1 mixture of regioisomers.

Workup

  1. temperatureAfter refluxing for 18 h
  2. temperaturethe reaction mixture was cooled down
  3. concentrationconcentrated at reduced pressure
  4. additionThe residue was treated with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialdried over magnesium sulphate
  7. concentrationThe organic layer was concentrated
  8. customthe residue was purified by flash-chromatography (methanol/methylene chloride, 0.5:9.5)
  9. customaffording 1.8 g (62%) of p-nitro-4 (5)-methyl-imidazol-1-yl
  10. additionas 7:1 mixture of regioisomers

Sources & evidence

ORD record
ord-607504fbb02144feb6755d4f21c8a597
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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