Ammonia → 5-Benzylidenehydantoin

HRID 67155

Reaction equation

HRID 67155 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

5

Reactant 4

HCID 222AmmoniaHCID 240BenzaldehydeHCID 1032Propionic AcidHCID 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.

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-b6bb45a4b7e84b40ba94557164a9d2d0
Source dataset
uspto-grants-1982_08
Patent number
US04345072

Linked notes

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