Acetic Acid → 4-Nitro-benzylidene-hydantoin

HRID 67156

Reaction equation

HRID 67156 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([O-:10])=[O:9].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(O)CCC>[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:7]2[NH:1][C:2](=[O:3])[NH:4][C:5]2=[O:6])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 10006HydantoinHCID 517165Ammonium Acetate

Product 1

HCID 46859054-Nitro-benzylidene-hydantoinYield 93.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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.

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-7fefe04751574bbd82fd98bf15e2f617
Source dataset
uspto-grants-1982_08
Patent number
US04345072

Linked notes

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