3-Methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline → 3-Methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione

HRID 34547Notes

Reaction equation

HRID 34547 reaction equation
[CH3:1][N:2]1[C:11](O)([C:12]([NH:14][C:15]([NH2:17])=[O:16])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:19]>ClC1C=CC=CC=1Cl>[CH3:1][N:2]1[C:11]2([C:12](=[O:13])[NH:14][C:15](=[O:16])[NH:17]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:19]

Participants

3

Reactant 1

HCID 142299933-Methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline

Product 1

HCID 142299883-Methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trioneYield 57.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

3-Methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline (1.5 g) is added to 1,2-dichlorobenzene (30 ml), and the mixture is refluxed with stirring for 1.5 hour. After cooling, the precipitates are taken by filtration and recrystallized from dimethylsulfoxide to give 3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (0.8 g).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe precipitates are taken by filtration
  4. customrecrystallized from dimethylsulfoxide

Sources & evidence

ORD record
ord-b3336cdeac09464d88e60add59210f36
Source dataset
uspto-grants-1988_08
Patent number
US04762839

Reaction notes

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