Isopropyl isocyanate → 1-N-i-Propylcarbamoyloxindole

HRID 4480

Reaction equation

HRID 4480 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-Propylcarbamoyloxindole

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, m.p. 84°-85.5° C., as pink crystals.

Workup

  1. additionTo a stirred suspension of 5.0 g
  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
  8. customgiving 7.0 g

Sources & evidence

ORD record
ord-2dd8beb060374261b699a38de66f5256
Source dataset
uspto-grants-1988_02
Patent number
US04725616

Linked notes

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