Phosphorus pentachloride → 5-Acetylamino-7,8-difluoro-1-tetralone

HRID 1683497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683497
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[C:7]2[C:6]=1[CH2:13][CH2:14][CH2:15][C:16]2=[O:18])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 105872254-(2-Acetylamino-4,5-difluorophenyl)butanoic acid

Produkt 1

HCID 224495485-Acetylamino-7,8-difluoro-1-tetralone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound obtained in (4) above (9.07 gm) was dissolved into 450 ml of dichloromethane. To the mixture was added 7.71 gm of phosphorous pentachloride while stirring at room temperature. After stirring for a further 1 hour, the reaction mixture was concentrated and dichloromethane was added to the residue. Dichloromethane was evaporated again and 500 ml of 1,2-dichloroethane and 9.88 gm of anhydrous aluminum chloride were added to the residue. The mixture was stirred for 1 hour at 70° C. and gently heated under reflux for 15 hours. The reaction product was poured into ice-cold water, extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography using chloroform-methanol (50:1) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to obtain 2.31 gm of the title compound.

Aufarbeitung

  1. stirringAfter stirring for a further 1 hour
  2. concentrationthe reaction mixture was concentrated
  3. additiondichloromethane was added to the residue
  4. customDichloromethane was evaporated again
  5. addition500 ml of 1,2-dichloroethane and 9.88 gm of anhydrous aluminum chloride were added to the residue
  6. stirringThe mixture was stirred for 1 hour at 70° C.
  7. temperaturegently heated
  8. temperatureunder reflux for 15 hours
  9. additionThe reaction product was poured into ice-cold water
  10. extractionextracted with chloroform
  11. washwashed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated
  14. customto obtain fractions
  15. additioncontaining the target compound
  16. concentrationThe fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-da33a204c88143cb83611841f0620bc7
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05637770

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