Ethyl Acetate → 1-benzyl-3,3-bis(N'-(4-methylphenyl)ureido)indolin-2-one

HRID 1533705Notes

Reaction equation

HRID 1533705 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](OC)(OC)[C:13]1=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH2:35])=[O:34])=[CH:28][CH:27]=1.C(O[CH2:41][CH3:42])(=O)C>O1CCCC1>[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([NH:35][C:33]([NH:32][C:29]2[CH:30]=[CH:31][C:41]([CH3:42])=[CH:27][CH:28]=2)=[O:34])([NH:35][C:33]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=2)=[O:34])[C:13]1=[O:25])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12148N-(4-Methylphenyl)ureaHCID 6451240Aluminum(III) ChlorideHCID 154582081-Benzyl-3,3-dimethoxyindolin-2-one

Product 1

HCID 98928581-benzyl-3,3-bis(N'-(4-methylphenyl)ureido)indolin-2-oneYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.80 g of anhydrous aluminum chloride in 20 ml of dry tetrahydrofuran were added successively a solution of 0.57 g of 1-benzyl-3,3-dimethoxyindolin-2-one in 10 ml of dry tetrahydrofuran and 0.60 g of p-tolylurea at 0° C. under a nitrogen atmosphere, and the mixture was heated under reflux for 2 hours. 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. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate=4/1) to obtain 0.24 g (23%) of 1-benzyl-3,3-bis(N′-(4-methylphenyl)ureido)indolin-2-one as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  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. customThe residue was purified by silica gel column chromatography (chloroform/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-52d0bbb328a341c2a757afa2b89aef8c
Source dataset
uspto-grants-2001_03
Patent number
US06207836B1

Reaction notes

Loading…