3-Phenylprop-2-Enal → 5-Cinnamylidenebarbituric acid

HRID 1703628Notes

Reaction equation

HRID 1703628 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:10](=O)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[CH:10](=[C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][C:8]1=[O:9])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 6211Barbituric Acid

Product 1

HCID 319075-Cinnamylidenebarbituric acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Barbituric acid (10.0 g) was dissolved in water (150 ml) at reflux, and the solution was stirred vigorously and maintained at just below refluxing point while freshly distilled cinnamaldehyde (10.3 g) was added slowly: a yellow precipitate formed almost immediately. After the addition, the mixture was stirred and maintained at just below refluxing point for 1 hour to complete the reaction. The product was filtered off, washed several times with hot water and then with cold ethanol, and then dried to give yellow 5-cinnamylidenebarbituric acid (18 g, 96% theoretical yield) m.p. 268°-70° (decomp).

Workup

  1. temperatureat reflux
  2. temperaturemaintained at just
  3. additionwas added slowly
  4. customa yellow precipitate formed almost immediately
  5. additionAfter the addition
  6. stirringthe mixture was stirred
  7. temperaturemaintained at just
  8. temperaturebelow refluxing point for 1 hour
  9. customthe reaction
  10. filtrationThe product was filtered off
  11. washwashed several times with hot water
  12. dry with materialwith cold ethanol, and then dried

Sources & evidence

ORD record
ord-bf6416d54efc46fa958ac508dacac7a3
Source dataset
uspto-grants-1978_11
Patent number
US04124760

Reaction notes

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