Reaction #95434

ord-7fefe04751574bbd82fd98bf15e2f617

Reaction equation

O=C1CNC(=O)N1
hydantoin
O=Cc1ccc([N+](=O)[O-])cc1
4-nitrobenzaldehyde
CC(=O)[O-].[NH4+]
ammonium acetate
CC(=O)O
acetic acid
→
O=C1NC(=O)C(=Cc2ccc([N+](=O)[O-])cc2)N1
5-(4'-nitrobenzylidene)-hydantoin
Yield 93.9%

Reactants

O=C1CNC(=O)N1
hydantoin
O=Cc1ccc([N+](=O)[O-])cc1
4-nitrobenzaldehyde
CC(=O)[O-].[NH4+]
ammonium acetate
CC(=O)O
acetic acid

Reagents

None

Solvents

CCCCO
n-butanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureat reflux temperature

Procedure

A mixture of 100 grams (1.0 mole) of hydantoin, 151 grams (1.0 mole) of 4-nitrobenzaldehyde, 77 grams (1.0 mole) of ammonium acetate, 120 grams (2.0 moles) of acetic acid, and 200 ml of n-butanol were held for 3 hours at reflux temperature. After the cooling, there were obtained 219 grams of 5-(4'-nitrobenzylidene)-hydantoin, corresponding to 94% of the theory based on hydantoin. The product had a melting point of 253°-254° C. and homogeneous by thin layer chromatography.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04345072uspto-grants-1982_08