Benzoylacetone → HCID 14098186, compound

HRID 622092Notes

Reaction equation

HRID 622092 reaction equation
[C:1]([CH2:9][C:10]([CH3:12])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:15](OC)[N:16](C)[CH3:17]>>[CH3:15][N:16]([CH3:17])[CH:9]([C:10](=[O:11])[CH3:12])[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

3

Reactant 2

HCID 7166BenzoylacetoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 14098186HCID 14098186, compoundYield 78%

Procedure

A mixture of 1-benzoylacetone (24.00 g, 0.15 mole) and dimethylformamide dimethylacetal were stirred overnight at room temperature under argon. The resulting reddish-colored mixture was concentrated on the rotary evaporator, then dissolved in THF (tetrahydrofuran). The resulting solution was stirred and heated to boiling the slowly diluted with hexane. At the point of turbidity heating was discontinued. An orange gum precipitated and rapidly solidified. The mixture was chilled in an ice bath and filtered yielding 25.5 g (78%) of 2-(dimethylamino)-1-phenyl-1,3-butanedione m.pt. 72°-74° C.

Workup

  1. concentrationThe resulting reddish-colored mixture was concentrated on the rotary evaporator
  2. dissolutiondissolved in THF (tetrahydrofuran)
  3. stirringThe resulting solution was stirred
  4. temperatureheated
  5. additionslowly diluted with hexane
  6. temperatureAt the point of turbidity heating
  7. customAn orange gum precipitated
  8. temperatureThe mixture was chilled in an ice bath
  9. filtrationfiltered

Sources & evidence

ORD record
ord-10b40d32268c4facad4ce8de06930811
Source dataset
uspto-grants-1988_09
Patent number
US04769380

Reaction notes

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