Benzaldehyde → 5-Benzylidenehydantoin

HRID 67154

Reaction equation

HRID 67154 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.[NH4+].C(O)=O>>[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 240BenzaldehydeHCID 284Formic AcidHCID 10006HydantoinHCID 2723923Ammonium formate

Product 1

HCID 978575-BenzylidenehydantoinYield 91.9%

Procedure

A mixture of 100 grams (1.0 mole) of hydantoin, 106 grams (1.0 mole) of benzaldehyde, 63 grams (1.0 mole) of ammonium formate, and 230 grams (5.0 moles) of formic acid were held for 3 hours at reflux temperature. After the cooling off, there were obtained 173 grams of 5-benzylidene hydantoin, corresponding to 92% of theory based on hydantoin.

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-b37aacc2f732407fb601b0a860bba435
Source dataset
uspto-grants-1982_08
Patent number
US04345072

Linked notes

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