Phenylurea → 1-phenylimidazolidine-2,4,5-trione

HRID 1578470Notes

Reaction equation

HRID 1578470 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13]>O1CCCC1>[C:1]1([N:7]2[C:12](=[O:13])[C:11](=[O:15])[NH:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6145PhenylureaHCID 65578Oxalyl chloride

Product 1

HCID 5772591-phenylimidazolidine-2,4,5-trione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

272.3 g of N-phenylurea are dissolved in 1.5 liters of tetrahydrofuran. The solution is heated to 50°C and slowly treated with 171 ml of oxalyl chloride, in the course of which the reaction temperature should not exceed 65°C. Stirring is continued for 1 hour at room temperature and then for 4 hours under reflux. The reaction mixture is evaporated and the residue is recrystallised from isopropanol to give 1-phenyl-2,4,5-trioxo-imidazolidine (m.p. 214°-216°C).

Workup

  1. customexceed 65°C
  2. temperaturefor 4 hours under reflux
  3. customThe reaction mixture is evaporated
  4. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-408c5130fddb424e94f9f2f26ce5d17f
Source dataset
uspto-grants-1976_02
Patent number
US03937626

Reaction notes

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