Oxindole → N-cyclohexylcarbonyl-2-oxindole-1-carboxamide

HRID 637360Notes

Reaction equation

HRID 637360 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]1([C:17]([N:19]=[C:20]=[O:21])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[CH:11]1([C:17]([NH:19][C:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][C:2]2=[O:10])=[O:21])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 321710OxindoleHCID 20096062Cyclohexanecarbonyl isocyanate

Product 1

HCID 13647650N-cyclohexylcarbonyl-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred slurry of 20.0 g (0.15 mole) of 2-oxindole in 150 ml of toluene was added 29.6 g (0.19 mole) of cyclohexylcarbonyl isocyanate. The mixture was heated under reflux for ca. 30 minutes and then it was cooled to room temperature. The solid was recovered by filtration and then it was recrystallized from ethanol. This afforded 26.5 g of the title compound as fluffy, colorless crystals, m.p. 144.5°-145.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for ca. 30 minutes
  3. filtrationThe solid was recovered by filtration
  4. customit was recrystallized from ethanol

Sources & evidence

ORD record
ord-893367bcce604dbfb9515c860ba36956
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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