Dibenzoylmethane → 2-[(Dimethylamino)methylidene]-1,3-diphenylpropane-1,3-dione

HRID 1170460Notes

Reaction equation

HRID 1170460 reaction equation
[C:1]([CH2:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[CH3:20][N:21]([CH:23]=[C:9]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:17])[CH3:22]

Participants

4

Reactant 2

HCID 8433DibenzoylmethaneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 130707692-[(Dimethylamino)methylidene]-1,3-diphenylpropane-1,3-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of dibenzoylmethane (1.072 g, 4.78 mmol) in 6 mL of toluene was added neat N,N-dimethylformamide dimethylacetal (0.7 mL, 630 mg, 5.25 mmol) dropwise via syringe. The resulting solution was stirred at rt for 1 h and then heated at reflux for 16 h. Once at rt, the reaction was concentrated in vacuo. The residue was dissolved in a minimum of CH2Cl2 and added to 13 cm of flash silica gel in a 5 cm dia. column. Elution with 1 L of 1%, 500 mL of 2% and 300 mL of 3% MeOH/CH2Cl2 gave 975 mg of the desired product as a semisolid. Trituration with 50 mL of hexanes gave 772 mg of the title compound as a light yellow solid, mp 123-124° C. (lit mp 120° C., Schenone, P. et al. J. Het. Chem. 1982,19(6), 1355-61).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. concentrationOnce at rt, the reaction was concentrated in vacuo
  4. dissolutionThe residue was dissolved in a minimum of CH2Cl2
  5. additionadded to 13 cm of flash silica gel in a 5 cm dia
  6. washElution with 1 L of 1%, 500 mL of 2% and 300 mL of 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-26ee4f71b68143ce834ba2cd60dbd108
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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