Water → HCID 66746000, compound

HRID 1810114Notes

Reaction equation

HRID 1810114 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[C:10]([OH:12])[CH:9]=[N:8]2)=[CH:3][CH:2]=1.[H-].[Na+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.O>CN(C)C=O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:12][C:10]2[CH:9]=[N:8][N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=3)[CH:11]=2)=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 129010791-(4-Methylphenyl)-1H-pyrazol-4-ol

Product 1

HCID 66746000HCID 66746000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-p-Tolyl-1H-pyrazol-4-ol (1.0 g, 5.75 mmol) in dimethylformamide was added to the cold slurry of sodium hydride (344 mg, 8.61 mmol). Reaction mixture was stirred for 0.5 hour followed by addition of 4-fluoro nitro benzene (810 mg, 5.74 mmol) in cold condition. Reaction mixture was stirred at 20-35° C. for 20 minutes. Water was then added to quench the reaction. The aqueous layer was extracted with diethylether and the combined organic layer was washed with brine solution and dried over anhydrous Na2SO4. The solvent was evaporated under vacuum at 40° C. and the product was purified by column chromatography using mixture of petroleum ether and ethyl acetate.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. stirringwas stirred at 20-35° C. for 20 minutes
  4. customto quench
  5. customthe reaction
  6. extractionThe aqueous layer was extracted with diethylether
  7. washthe combined organic layer was washed with brine solution
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was evaporated under vacuum at 40° C.
  10. customthe product was purified by column chromatography
  11. additionmixture of petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-64aa9454335b405aaa28be6074589032
Source dataset
uspto-grants-2013_01
Patent number
US08362064B2

Reaction notes

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