Isatin → 1-Benzylisatin

HRID 365981ノート

反応式

HRID 365981 の反応式
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 7054IsatinHCID 7498Benzyl BromideHCID 24758Sodium hydride

生成物 1

HCID 2647341-Benzylisatin収率 67%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 44 g of isatin in 200 ml of N,N-dimethylformamide was added dropwise to a suspension of 16.0 g of sodium hydride (60%) in 100 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After the mixture was stirred at that temperature for 30 minutes, a solution of 61.5 g of benzyl bromide in 100 ml of N,N-dimethylformamide was added thereto. The whole mixture was stirred for 1 hour and then concentrated. Chloroform was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was washed with hexane and recrystallized from ethanol to give 47.3 g (67%) of the title compound as red needles.

後処理

  1. stirringThe whole mixture was stirred for 1 hour
  2. concentrationconcentrated
  3. additionChloroform was added to the residue
  4. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washThe resulting crude product was washed with hexane
  8. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-c1a6a6add9334a1589d1f65ee9061472
出典データセット
uspto-grants-2000_10
特許番号
US06127544

反応ノート

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