Dimethylformamide → 1,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde

HRID 1851096Notes

Reaction equation

HRID 1851096 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9](=[O:18])[N:8]1[CH3:19].[OH-].[Na+].CN([CH:25]=[O:26])C>O>[CH3:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([CH:25]=[O:26])[C:9](=[O:18])[N:8]1[CH3:19]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 155598371,2-Dimethyl-5-phenyl-1,2-dihydro-3H-pyrazol-3-one

Product 1

HCID 583683381,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Dimethylformamide (3.4 mL, 43.6 mmol) was added to a flask under nitrogen atmosphere. After cooling to 0° C., phosphorus oxychloride (1.4 mL, 15.2 mmol) was added. The resulting reaction mixture was stirred at room temperature for 50 minutes. The resulting reaction mixture was transferred to a reaction flask containing a solution of 1,2-dimethyl-5-phenyl-1H-pyrazol-3(2H)-one (820 mg, 4.36 mmol) in DMF (4.9 mL). The reaction flask was immersed in a preheated oil bath (120° C.) and, after stirring for 12 minutes, cooled to room temperature. 5 N NaOH (15 mL) was added to the cooled reaction mixture. After diluting with icy water, the mixture was extracted with chloroform. The organic layer was dried with sodium sulfate and then filtered. The filtrate was concentrated. After diluting DMF remaining in the resulting residue again with chloroform and then washing with water, the aqueous layer was extracted again with chloroform. The organic layer was collected, dried with sodium sulfate, and then filtered. The filtrate was concentrated. The concentrated residue was subjected to the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. customwas transferred to a reaction flask
  4. customThe reaction flask was immersed in a preheated oil bath
  5. stirring(120° C.) and, after stirring for 12 minutes
  6. temperaturecooled to room temperature
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. additionAfter diluting DMF remaining in the resulting residue again with chloroform
  12. washwashing with water
  13. extractionthe aqueous layer was extracted again with chloroform
  14. customThe organic layer was collected
  15. dry with materialdried with sodium sulfate
  16. filtrationfiltered
  17. concentrationThe filtrate was concentrated
  18. customThe concentrated residue was subjected to the next step without further purification

Sources & evidence

ORD record
ord-e4dbb6a91ea24352be8ad73e2d9d4b58
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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