Chlorosulfonyl isocyanate → 5-Benzoyl-2-oxindole-1-carboxamide

HRID 978688Notes

Reaction equation

HRID 978688 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:23]=[C:24]=[O:25])(=O)=O>O1CCCC1>[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:24]([NH2:23])=[O:25])[C:13](=[O:18])[CH2:12]2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 134081645-Benzoyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 136476435-Benzoyl-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.1 g. (42 mmole) of 5-benzoyl-2-oxindole, 4.4 ml. (51 mmole) of chlorosulfonyl isocyanate and 300 ml. of tetrahydrofuran was stirred at room temperature for 6 hours, and then the solvent was removed by evaporation in vacuo. The residue was added to 150 ml. of glacial acetic acid and 300 ml. of water and the resulting mixture was heated under reflux for 2 hours. The reaction mixture was cooled and the supernatant liquid was removed by decantation. The remaining gummy residue was triturated under acetonitrile to give a solid which was recovered by filtration and then recrystallized from a 1:1 mixture of n-propanol and acetonitrile. This gave 4.1 g. of the title compound as a solid, mp. 210°-211° C.

Workup

  1. additionA mixture of 10.1 g
  2. customthe solvent was removed by evaporation in vacuo
  3. additionThe residue was added to 150 ml
  4. temperatureof water and the resulting mixture was heated
  5. temperatureunder reflux for 2 hours
  6. temperatureThe reaction mixture was cooled
  7. customthe supernatant liquid was removed by decantation
  8. customThe remaining gummy residue was triturated under acetonitrile
  9. customto give a solid which
  10. filtrationwas recovered by filtration
  11. customrecrystallized from a 1:1 mixture of n-propanol and acetonitrile

Sources & evidence

ORD record
ord-77f810741f44465babf57c2a41dd13be
Source dataset
uspto-grants-1987_05
Patent number
US04665194

Reaction notes

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