Isopropyl isocyanate → 1-N-i-Propylcarbamoyloxindole

HRID 1589383Notes

Reaction equation

HRID 1589383 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11]([N:14]=[C:15]=[O:16])([CH3:13])[CH3:12]>C1(C)C=CC=CC=1>[CH:11]([NH:14][C:15]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10])=[O:16])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 321710Oxindole

Product 1

HCID 135656731-N-i-PropylcarbamoyloxindoleYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 5.0 g (37.6 mmole) of 2-oxindole in 50 ml of toluene was added 8.0 g (94.0 mmole) of isopropyl isocyanate, and the mixture was heated under reflux for 6 hours. The reaction mixture was allowed to cool and then it was stirred at room temperature overnight. The solvent was removed by evaporation in vacuo, and the residue was dissolved in hot cyclohexane. The solution was allowed to cool and the solid was collected by filtration, giving 7.0 g of the title compound, mp 84°-85.5° C., as pink crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool
  4. customThe solvent was removed by evaporation in vacuo
  5. dissolutionthe residue was dissolved in hot cyclohexane
  6. temperatureto cool
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-6a442c4003c44daeb58d6b9920334144
Source dataset
uspto-grants-1986_02
Patent number
US04569942

Reaction notes

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