3,5-Dimethylpyrazole → HCID 178463127, compound

HRID 1738357Notes

Reaction equation

HRID 1738357 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[H-].[Na+].[CH2:10]([N:12]1[C:16]([OH:17])=[C:15]([C:18](=[O:31])[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[C:21](F)[C:20]=2[Cl:30])[CH:14]=[N:13]1)[CH3:11]>CN(C)C=O>[CH2:10]([N:12]1[C:16]([OH:17])=[C:15]([C:18](=[O:31])[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[C:21]([N:3]3[C:2]([CH3:1])=[CH:6][C:5]([CH3:7])=[N:4]3)[C:20]=2[Cl:30])[CH:14]=[N:13]1)[CH3:11]

Participants

5

Reactant 3

HCID 62103,5-DimethylpyrazoleHCID 24758Sodium hydrideHCID 178463121HCID 178463121, compound

Product 1

HCID 178463127HCID 178463127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3,5-Dimethylpyrazole (215 mg, 2.23 mmol) was added to a suspension of 150 mg (3.75 mmol) of 60 percent oil dispersed sodium hydride in 6 mL of dry dimethylformamide. After gas evolution had subsided, 500 mg (1.45 mmol) of 1-ethyl-4-(2-chloro-3-fluoro-4-methylsulfonylbenzoyl)-5-hydroxypyrazole was added and the mixture was stirred at 50° C. overnight. The reaction mixture was concentrated by evaporation under reduced pressure and partitioned between dichloromethane and 1N aqueous hydrochloric acid. The aqueous phase was extracted with additional dichloromethane. The organic layers were combined and extracted with dilute aqueous sodium bicarbonate. The aqueous extract was acidified with 1N aqueous hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The solvent was removed from the organic extract by evaporation under reduced pressure and the crystalline residue obtained was purified by rinsing with diethyl ether to obtain 360 mg (59 percent of theory) of the title compound as a white powder melting at 217-218° C.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  2. custompartitioned between dichloromethane and 1N aqueous hydrochloric acid
  3. extractionThe aqueous phase was extracted with additional dichloromethane
  4. extractionextracted with dilute aqueous sodium bicarbonate
  5. extractionThe aqueous extract
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. customThe solvent was removed from the
  8. extractionorganic extract by evaporation under reduced pressure
  9. customthe crystalline residue obtained
  10. customwas purified
  11. washby rinsing with diethyl ether

Sources & evidence

ORD record
ord-467a71a58b624051958889ba707dcf88
Source dataset
uspto-grants-1999_10
Patent number
US05962690

Reaction notes

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