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

HRID 1953304노트

반응식

HRID 1953304 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5ea18534cc23408d8eeee40af9cc7a1d
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06114536

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