Benzoyl isocyanate → HCID 13910502, compound

HRID 542593Notes

Reaction equation

HRID 542593 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].[C:11]([N:19]=[C:20]=[O:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[C:11]([NH:19][C:20]([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:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 321710Oxindole

Product 1

HCID 13910502HCID 13910502, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred slurry of 399 mg (3.0 mmole) of 2-oxindole in 7 ml of toluene was added 485 mg (3.3 mmole) of benzoyl isocyanate. The mixture was heated under reflux for 2.2 hours and then it was cooled to room temperature. The solid was recovered by filtration and it was then dissolved in ca. 10 ml of hot acetonitrile. The acetonitrile solution was decolorized using activated carbon and then allowed to cool and the precipitate was recovered by filtration. Recrystallization of the precipitate from acetonitrile gave 131 mg of the title compound, mp 183.5°-184.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.2 hours
  3. filtrationThe solid was recovered by filtration and it
  4. dissolutionwas then dissolved in ca. 10 ml of hot acetonitrile
  5. temperatureto cool
  6. filtrationthe precipitate was recovered by filtration
  7. customRecrystallization of the precipitate from acetonitrile

Sources & evidence

ORD record
ord-2b34e4640e61423e9180c2186802c1e9
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Reaction notes

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