5-Chlorooxindole → N-isobutyryl-5-chloro-2-oxindole-1-carboxamide

HRID 637361Notes

Reaction equation

HRID 637361 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:12]([N:17]=[C:18]=[O:19])(=[O:16])[CH:13]([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[C:12]([NH:17][C:18]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:11])=[O:19])(=[O:16])[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 1528015-ChlorooxindoleHCID 127486372-Methylpropanecarbonyl isocyanate

Product 1

HCID 13647652N-isobutyryl-5-chloro-2-oxindole-1-carboxamideYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred slurry of 8.38 g (0.05 mole) of 5-chloro-2-oxindole in 250 ml of toluene was added 6.79 g (0.06 mole) of isobutyryl isocyanate, and the reaction mixture was heated under reflux for 5.5 hours. The reaction mixture was cooled to room temperature, a small amount of insoluble material was removed by filtration, and then the solvent was removed by evaporation in vacuo. The residue was recrystallized from acetonitrile (with the aid of decolorizing carbon), followed by recrystallization from ethanol, to give 3.23 g of the title compound as pink crystals, m.p. 139°-141° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5.5 hours
  3. customa small amount of insoluble material was removed by filtration
  4. customthe solvent was removed by evaporation in vacuo
  5. customThe residue was recrystallized from acetonitrile (with the aid of decolorizing carbon),
  6. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-4141470d1ce646a6b2d9c4e9de47d987
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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