2-Ethylhexanoic Acid → 1-Benzyl-3-phenyl-5-(methoxycarbonylmethylene)-hydantoin

HRID 372163

Reaction equation

HRID 372163 reaction equation
[C:1]1([NH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C(CCCC)C(O)=O)C.[C:28](OC)(=[O:35])/[CH:29]=[CH:30]\[C:31]([O:33][CH3:34])=[O:32]>ClC1C=CC=CC=1Cl>[CH2:11]([N:10]1[C:29](=[CH:30][C:31]([O:33][CH3:34])=[O:32])[C:28](=[O:35])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]1=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 86972-Ethylhexanoic AcidHCID 2803631-Benzyl-3-phenylureaHCID 5271565Dimethyl maleate

Product 1

HCID 545354751-Benzyl-3-phenyl-5-(methoxycarbonylmethylene)-hydantoin

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

113 g of N-phenyl-N'-benzyl-urea were dissolved in 1000 g of o-dichlorobenzene; the solution was made acid with 2-ethyl-hexanoic acid and reacted with 72 g of dimethyl maleate. After a reaction time of 6 hours at 175° C, the solvent was distilled off and the residue triturated with ether. The product separated by suction filtration can be obtained pure by recrystallisation from toluene. The white crystals obtained have a melting point of 130° C and their structure was demonstrated by the IR and NMR spectra and elementary analysis.

Workup

  1. distillationAfter a reaction time of 6 hours at 175° C, the solvent was distilled off
  2. customthe residue triturated with ether
  3. customThe product separated by suction filtration
  4. customcan be obtained pure by recrystallisation from toluene
  5. customThe white crystals obtained

Sources & evidence

ORD record
ord-90fb7d6c8dd344ceb2bd3aad678348e5
Source dataset
uspto-grants-1978_05
Patent number
US04089860

Linked notes

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