Urea → 3-Methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline

HRID 34553

Reaction equation

HRID 34553 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[C:6]1=[O:7])=[O:4].C1CCN2C(=NCCC2)CC1.[NH2:27][C:28]([NH2:30])=[O:29]>O1CCCC1>[CH3:1][N:2]1[C:8]([OH:9])([C:6]([NH:27][C:28]([NH2:30])=[O:29])=[O:7])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:5][C:3]1=[O:4]

Participants

5

Reactant 3

HCID 1176UreaHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2835543N-(methylcarbamoyl)isatin

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methylcarbamoylisatin (10.2 g) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.3 g) are dissolved in tetrahydrofuran (100 ml), and thereto is added urea (4.5 g), and the mixture is refluxed for 10 hours. After cooling, the precipitates are taken by filtration, washed with water and methanol and recrystallized from a mixture of dimethylsulfoxide and ethanol to give 3-methyl-4-hydroxy-4-ureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline, M.p.>280° C.,

Workup

  1. temperaturethe mixture is refluxed for 10 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitates are taken by filtration
  4. washwashed with water and methanol
  5. customrecrystallized from a mixture of dimethylsulfoxide and ethanol

Sources & evidence

ORD record
ord-ee11b7a4037446ff838830f2b1b77ab6
Source dataset
uspto-grants-1988_08
Patent number
US04762839

Linked notes

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