Benzoylacetone → HCID 22346892, compound

HRID 432501Notes

Reaction equation

HRID 432501 reaction equation
[C:1]([CH2:9][C:10]([CH3:12])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1>CO>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C:10]([CH3:12])=[N:31]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7166BenzoylacetoneHCID 121574-Bromophenylhydrazine hydrochlorideHCID 81531Diisopropylethylamine

Product 1

HCID 22346892HCID 22346892, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzoylacetone (3.63 g, 0.0224 mol) and N,N-diisopropylethylamine (2.88 g, 0.0224 mol) in anhydrous methanol (160 mL), 4-bromophenylhydrazine hydrochloride was added and the resulting mixture was stirred at ambient temperature for 20 hours. The solvent was removed under reduced pressure and the resulting mixture was partitioned between a 5% solution of citric acid solution in water (200 mL) and ethyl acetate (150 mL). The organic phase was successively washed with water (2×200 mL) and brine (150 mL), dried with magnesium sulfate and concentrated. The resulting residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (5:95) as mobile phase to yield 1-(4-bromophenyl)-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazole (4.05 g, 0.0129 mol) as an off-white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting mixture was partitioned between a 5% solution of citric acid solution in water (200 mL) and ethyl acetate (150 mL)
  3. washThe organic phase was successively washed with water (2×200 mL) and brine (150 mL)
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-9e1dc977dca84b0a9613128c2ad031f1
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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