Water → HCID 13647635, compound

HRID 978685Notes

Reaction equation

HRID 978685 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.ClS([N:19]=[C:20]=[O:21])(=O)=O.O>C(#N)C>[F:14][C:2]([F:1])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[N:9]2[C:20]([NH2:19])=[O:21])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 6084876-Trifluoromethyloxindole

Product 1

HCID 13647635HCID 13647635, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of 6-trifluoromethyl-2-oxindole (8.0 g, 0.04 mole) in acetonitrile (80 ml) was added chlorosulfonyl isocyanate (6.65 g, 0.047 mole) and the mixture stirred for 45 minutes. Water (100 ml) was then added and the aqueous mixture stirred for one hour. The precipitate which formed was filtered off and recrystallized from acetonitrile to give 0.92 g of title product. Extraction of the filtration 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 additional (2.2 g) product.

Workup

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

Sources & evidence

ORD record
ord-8170dc49913249f58dba4c06ecd936b6
Source dataset
uspto-grants-1987_05
Patent number
US04665194

Reaction notes

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