Ammonia → 5-Benzylidenehydantoin

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)CC.N>>[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

Reactant 4

HCID 222Ammonia

HCID 240Benzaldehyde

HCID 1032Propionic Acid

HCID 10006Hydantoin

Product 1

HCID 978575-BenzylidenehydantoinYield 94.6%

Procedure

To a mixture of 100 grams (1.0 mole) of hydantoin, 106 grams (1.0 mole) of benzaldehyde, and 370 grams (5.0 moles) of propionic acid, there were added 17 grams (1.0 mole) of ammonia. The mixture was subsequently held for 3 hours at reflux temperature. After the cooling off, there were obtained 178 grams of 5-benzylidene hydantoin, corresponding to 95% of theory based on hydantoin.