Potassium Fluoride → HCID 14071292, compound

HRID 1904746Notes

Reaction equation

HRID 1904746 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:17](=[O:18])[C:16]2=[C:19]([N+]([O-])=O)[CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:26])([CH3:3])[CH3:2].[F-:27].[K+]>CS(C)=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:17](=[O:18])[C:16]2=[C:19]([F:27])[CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:26])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 200380352-[2,6-Di(propan-2-yl)phenyl]-4-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 14071292HCID 14071292, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

In 300 ml of dimethylsulfoxide was dissolved 14.0 g of N-(2',6'-diisopropylphenyl)-3-nitrophthalimide, and 10.0 g of potassium fluoride was added to the solution. The mixture was heated on an oil bath at 100° C. for 3 hours. The liquid reaction mixture was concentrated under reduced pressure below 80° C., and the residue was extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried and concentrated. Then, 20 ml of methanol was added to the residue, and the mixture was cooled and allowed to stand still. The compound 3 was precipitated in the form of colorless crystals. The amount obtained of the crude product was 10.1 g, yield: 77.6%. The crude crystals were recrystallized from methanol two times to obtain 4.5 g of pure crystals.

Workup

  1. additionwas added to the solution
  2. customThe liquid reaction mixture
  3. concentrationwas concentrated under reduced pressure below 80° C.
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with water
  6. customdried
  7. concentrationconcentrated
  8. additionThen, 20 ml of methanol was added to the residue
  9. temperaturethe mixture was cooled
  10. customThe compound 3 was precipitated in the form of colorless crystals
  11. customThe amount obtained of the crude product
  12. customThe crude crystals were recrystallized from methanol two times

Sources & evidence

ORD record
ord-2e7c92a36c3e4151b4ed5cb4e6791379
Source dataset
uspto-grants-1989_06
Patent number
US04839378

Reaction notes

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