Water → HCID 23517202, compound

HRID 1633569Notes

Reaction equation

HRID 1633569 reaction equation
[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].C(=O)([O-])[O-].[K+].[K+].[C:18]([O:22][C:23](=[O:26])[CH2:24]Br)([CH3:21])([CH3:20])[CH3:19].O>CN(C=O)C>[C:18]([O:22][C:23](=[O:26])[CH2:24][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])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7054IsatinHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 23517202HCID 23517202, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44.1 g (0.3 mol) of isatin, 62.5 g (0.45 mol) of potassium carbonate and 66.2 g (0.34 mol) of bromoacetic acid tert-butyl ester (from Aldrich) are stirred in 100 ml of N,N′-dimethylformamide at room temperature for 24 hours. The mixture is then poured into 800 ml of water, and the precipitate formed is filtered off, washed with water and dried at 60° C. After recrystallising once from toluene-hexane (1:1), 608 g (78% of theory) of product having a melting point of 119-121° C. are obtained.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried at 60° C
  5. customAfter recrystallising once from toluene-hexane (1:1), 608 g (78% of theory) of product
  6. customare obtained

Sources & evidence

ORD record
ord-b47696d4fb2d407f8134372a3420b51d
Source dataset
uspto-grants-2003_01
Patent number
US06503937B1

Reaction notes

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