p-Fluoronitrobenzene → 2-[(4-Nitrophenyl)thio]-1-phenyl-1H-imidazole

HRID 1074196Notes

Reaction equation

HRID 1074196 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][N:8]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([S:3][C:4]2[N:5]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:7][N:8]=2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 178527866HCID 178527866, compound

Product 1

HCID 150774972-[(4-Nitrophenyl)thio]-1-phenyl-1H-imidazoleYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.6 g (13.6 mmoles) of 50% sodium hydride in mineral oil and 8 ml of N,N-dimethylformamide was added 2.0 g (11.4 mmoles) of 2-mercapto-1-phenylimidazole. After stirring for 10 minutes the mixture was cooled in an icebath and 2.1 g (14.8 mmoles) of 1-fluoro-4-nitrobenzene was added. After stirring for 20 minutes, the mixture was warmed to room temperature and stirred for 3 hours. Ice was added and the mixture partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The organics were dried and concentrated. The residue was recrystallized from dichloromethane/petroleum ether (bp 30°-60° C.) to give 0.9 g (27%) of the product as off-white prisms, mp 123°-125° C.

Workup

  1. additionwas added
  2. stirringAfter stirring for 20 minutes
  3. stirringstirred for 3 hours
  4. additionIce was added
  5. customthe mixture partitioned between dichloromethane and water
  6. customThe aqueous phase was separated
  7. extractionextracted with dichloromethane
  8. customThe organics were dried
  9. concentrationconcentrated
  10. customThe residue was recrystallized from dichloromethane/petroleum ether (bp 30°-60° C.)

Sources & evidence

ORD record
ord-096586a11b4e450495d4514d8d50d9c2
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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