Dimethylformamide → HCID 59438278, compound

HRID 604298Notes

Reaction equation

HRID 604298 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH:17]=[CH:16][C:15]([CH3:18])=[N:14]2)[CH:10]=[CH:11][CH:12]=1.CN(C)[CH:21]=[O:22].C(=O)([O-])O.[Na+]>>[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH:17]=[C:16]([CH:21]=[O:22])[C:15]([CH3:18])=[N:14]2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 17947723HCID 17947723, compound

Product 1

HCID 59438278HCID 59438278, compound

Conditions

Temperature
95 °C

Procedure

Add phosphorus oxychloride (20.8 mL, 34.3 g, 223.7 mmol) dropwise with stirring at 95° C. under nitrogen to 1-(3-fluoro-phenyl)-3-methyl-1H-pyrazole (4.38 g, 24.86 mmol) in dimethylformamide (19.2 mL, 18.17 g, 248.6 mmol). Heat at 95° C. for 15 hr., cool to room temperature, pour over ice and neutralize with sodium hydrogen carbonate. Extract the aqueous solution with ethyl acetate (2×150 mL), dry (magnesium sulfate), filter, and pass through an SCX-2 column. Evaporate the solvent to give 1-(3-fluoro-phenyl)-3-methyl-1H-pyrazole-4-carbaldehyde as a solid. (4.22 g, 83%). MS (m/z): 205.1 (M+1).

Workup

  1. temperature, cool to room temperature
  2. additionpour over ice
  3. extractionExtract the aqueous solution with ethyl acetate (2×150 mL)
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. customEvaporate the solvent

Sources & evidence

ORD record
ord-213755a9bc2d42fa93922482a0778b76
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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