Benzoyl isocyanate → N-Benzoyl-3-(2-furoyl)-2-oxindole-1-carboxamide

HRID 542588Notes

Reaction equation

HRID 542588 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17])=[O:7].[C:18]([N:26]=[C:27]=[O:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:18]([NH:26][C:27]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]([C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[C:9]1=[O:17])=[O:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 13565652HCID 13565652, compound

Product 1

HCID 13910498N-Benzoyl-3-(2-furoyl)-2-oxindole-1-carboxamideYield 61.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 909 mg (4.0 mmole) of 3-(2-furoyl)-2-oxindole and 706 mg (4.8 mmole) of benzoyl isocyanate in 25 ml of toluene was heated to reflux and then it was heated at reflux temperature for 7 hours. The mixture was allowed to stand at room temperature overnight and then the precipitate which had formed was removed by filtration, giving 1.3 g of crude product. The crude product was recrystallized from ca 30 ml of acetic acid, giving 920 mg of the title compound, mp 184° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureit was heated
  4. temperatureat reflux temperature for 7 hours
  5. customthe precipitate which had formed
  6. customwas removed by filtration
  7. customgiving 1.3 g of crude product
  8. customThe crude product was recrystallized from ca 30 ml of acetic acid

Sources & evidence

ORD record
ord-56a3a2ca034e4cb99b2a7017e6917435
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Reaction notes

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