Water → 6-Chloro-5-fluoro-2-oxo-1-indolinecarboxamide

HRID 487914

Reaction equation

HRID 487914 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[F:12].ClS([N:17]=[C:18]=[O:19])(=O)=O.O>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[N:8]2[C:18]([NH2:17])=[O:19])=[CH:4][C:3]=1[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 97940836-Chloro-5-fluoroindolin-2-one

Product 1

HCID 136476406-Chloro-5-fluoro-2-oxo-1-indolinecarboxamideYield 10.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of 6-chloro-5-fluoro-2-oxindole (0.04 mole) in acetonitrile (80 ml) was added chlorosulfonyl isocyanate (6.65 g, 0.047 mole) and the mixture was stirred for 45 minutes. Water (100 ml) was then added and the aqueous mixture was stirred for one hour. The precipitate which formed was filtered off and recrystallized from acetonitrile to give 0.92 g of the title product. Extraction of the filtrate from the aqueous reaction mixture with ethyl acetate (300 ml) followed by drying the extract over MgSO4 and then evaporating it under reduced pressure gave additional product. Recrystallization from acetonitrile gave an additional 2.2 g of product, m.p. 229°-231° C.

Workup

  1. stirringthe aqueous mixture was stirred for one hour
  2. customThe precipitate which formed
  3. filtrationwas filtered off
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c88dea8392d84c72ba162669590206a9
Source dataset
uspto-grants-1994_03
Patent number
US05298522

Linked notes

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