Chloroacetone → 1-(1-Phenyl-1H-pyrazol-5-yl)ethan-1-one

HRID 1747786Notes

Reaction equation

HRID 1747786 reaction equation
[C:1]1([NH:7][N:8]=[CH:9][CH:10]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20](=[O:22])[CH3:21]>O1CCOCC1>[C:1]1([N:7]2[C:19]([C:20](=[O:22])[CH3:21])=[CH:10][CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 2774401(2-Phenylhydrazinylidene)acetaldehyde

Product 1

HCID 534219791-(1-Phenyl-1H-pyrazol-5-yl)ethan-1-oneYield 34.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-(phenylhydrazono)ethanal (3.10 g) (Journal of Chemical Society, Perkin Trans. 1, 1981, 503-513.), potassium carbonate (4.40 g) and dioxane (20.0 mL) was added 1-chloropropan-2-one (2.10 g) at room temperature, and the mixture was heated under reflux for 5 hr. The reaction mixture was concentrated under reduced pressure and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (1.35 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-d83585c5f239434aa1cf5791c6808610
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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