Benzoylacetone → HCID 14098186, compound

HRID 1589267Notes

Reaction equation

HRID 1589267 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 and 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 25.25 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-83be1bc7628244089ca7a7dd2276df64
Source dataset
uspto-grants-1986_02
Patent number
US04568751

Reaction notes

Loading…