Trifluoroacetic anhydride → 2-Oxindole-1-carboxamide

HRID 637343Notes

Reaction equation

HRID 637343 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([OH:14])=O)[C:2]([NH2:4])=[O:3].FC(F)(F)C(OC(=O)C(F)(F)F)=O>FC(F)(F)C(O)=O>[N:1]1([C:2]([NH2:4])=[O:3])[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:11][C:12]1=[O:14]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 136476542-(2-Ureidophenyl)acetic acid

Product 1

HCID 115172742-Oxindole-1-carboxamideYield 34.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 194 mg (1.0 mmole) of 2-(2-ureidophenyl)acetic acid in 4 ml of trifluoroacetic acid was added 630 mg (3.0 mmole) of trifluoroacetic anhydride, and the mixture was then heated under reflux for ca. 1 hour. The reaction mixture was cooled and the solvent was removed by evaporation in vacuo. The residue was triturated under 5-8 ml of saturated sodium bicarbonate solution, and the material which remained out of solution was collected by filtration. The solid thus obtained was recrystallized from ethanol to give 61 mg of the title compound as colorless needles, m.p. 179°-180° C. (slight decomposition).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for ca. 1 hour
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed by evaporation in vacuo
  5. customThe residue was triturated under 5-8 ml of saturated sodium bicarbonate solution
  6. filtrationwas collected by filtration
  7. customThe solid thus obtained
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-d1bc9c1dc6d649c494a22895e0533e3e
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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