Benzaldehyde → 5-Benzylidenehydantoin

HRID 1380624Notes

Reaction equation

HRID 1380624 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH:8](=[C:7]1[NH:1][C:2](=[O:3])[NH:4][C:5]1=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10006HydantoinHCID 517165Ammonium Acetate

Product 1

HCID 978575-BenzylidenehydantoinYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Similar to the procedure of U.S. Pat. No. 4,345,072, a mixture comprising hydantoin (25 g, 0.25 mole), benzaldehyde (29.3 g, 0.275 mole), ammonium acetate (19.3 g, 0.25 mole) and glacial acetic acid (60 g) were placed in a round bottom flask fitted with stirrer, condenser, thermometer and heating mantle. The white solids became yellow on heating. All the solids dissolved when the temperature reached between 120° C. and 134° C. The mixture was refluxed for one-half hour (125° to 134° C.) and then held at 120° C. for 4 hours with stirring. Solids crystallized out on cooling to room temperature. The solid was suction filtered, water washed and then ethanol washed. After air drying, the yellow orange solid had a weight of 38.0 g for an 81% yield. The melting point of the 5-benzalhydantoin obtained was determined to be 218°-220° C. which corresponds to the melting point reported in BIOCHEM J. 29, 542 (1935).

Workup

  1. customfitted with stirrer, condenser
  2. temperaturethermometer and heating mantle
  3. temperatureon heating
  4. dissolutionAll the solids dissolved when the temperature
  5. customreached between 120° C. and 134° C
  6. temperatureThe mixture was refluxed for one-half hour (125° to 134° C.)
  7. customSolids crystallized out
  8. filtrationfiltered
  9. washwater washed
  10. washethanol washed
  11. customAfter air drying

Sources & evidence

ORD record
ord-d775eca4a8fe4d189d791c7b2cdbe06b
Source dataset
uspto-grants-1986_04
Patent number
US04582903

Reaction notes

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