Beta-Alanine → 5-(p-Methoxybenzylidene)-hydantoin

HRID 1763738Notes

Reaction equation

HRID 1763738 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[O:13].NCCC(O)=O>C(O)(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[C:17]2[NH:11][C:12](=[O:13])[NH:14][C:15]2=[O:16])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 10006HydantoinHCID 312444-Methoxybenzaldehyde

Product 1

HCID 947495-(p-Methoxybenzylidene)-hydantoin

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 136 g of p-anisaldehyde, 110 g. of hydantoin and 20 g. of β-alanine in 400 ml. of acetic acid is heated under reflux for seven hours. After a short period at reflux a clear solution is obtained; however, a solid appears after a few hours. The mixture is stirred at room temperature overnight, diluted with 400 ml. of water, filtered and the solid washed first with methanol and next with water. The solid is then slurried in 1.5 liters of boiling ethanol and filtered while still hot. The solid is dried in a vacuum oven to give the above named compound as a bright yellow solid, mp. 250°-253° C.

Workup

  1. temperatureunder reflux for seven hours
  2. temperatureAfter a short period at reflux a clear solution
  3. customis obtained
  4. waithowever, a solid appears after a few hours
  5. additiondiluted with 400 ml
  6. filtrationof water, filtered
  7. washthe solid washed first with methanol and next with water
  8. filtrationfiltered while still hot
  9. customThe solid is dried in a vacuum oven
  10. customto give the

Sources & evidence

ORD record
ord-1c8678e16e3b48238dcd398c129a1bfd
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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