Ethyl Acetate → 3,3-Bis(N'-(4-methylphenyl)ureido)indolin-2-one

HRID 1533706Notes

Reaction equation

HRID 1533706 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH2:14])=[O:13])=[CH:7][CH:6]=1.C([O:19][CH2:20][CH3:21])(=O)C>O1CCCC1>[CH3:15][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:13])[NH:14][C:21]2([NH:14][C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=3)=[O:13])[C:9]3[C:8](=[CH:7][CH:6]=[CH:5][CH:10]=3)[NH:11][C:20]2=[O:19])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12148N-(4-Methylphenyl)ureaHCID 6451240Aluminum(III) Chloride

Product 1

HCID 99323753,3-Bis(N'-(4-methylphenyl)ureido)indolin-2-oneYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 12.0 g of anhydrous aluminum chloride in 150 ml of dry tetrahydrofuran were added successively a solution of 5.79 g of isatin-3,3-dimethylacetal in 150 ml of dry tetrahydrofuran and 9.0 g of p-tolylurea at 0° C. under a nitrogen atmosphere, and the mixture was heated under reflux for 40 minutes. Ethyl acetate was added to the reaction mixture, and the mixture was washed twice with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate, followed by concentration. To the residue was added 150 ml of ethyl ether, and insoluble matter was removed by filtration. The filtrate was concentrated and recrystallized from acetone to yield 4.61 g (36%) of the title compound as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 minutes
  3. washthe mixture was washed twice with an aqueous solution of sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration
  6. additionTo the residue was added 150 ml of ethyl ether, and insoluble matter
  7. customwas removed by filtration
  8. concentrationThe filtrate was concentrated
  9. customrecrystallized from acetone

Sources & evidence

ORD record
ord-c5597bf53fbb4a0bb1a9dae8acaba9e5
Source dataset
uspto-grants-2001_03
Patent number
US06207836B1

Reaction notes

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