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

HRID 1533705ノート

反応式

HRID 1533705 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-52d0bbb328a341c2a757afa2b89aef8c
出典データセット
uspto-grants-2001_03
特許番号
US06207836B1

反応ノート

読み込み中…