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

HRID 1953304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953304
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5ea18534cc23408d8eeee40af9cc7a1d
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06114536

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