p-Toluenesulfonic acid → 3,6-difluoro-N-isobutylphthalimide

HRID 733257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733257
[F:1][C:2]1[CH:12]=[CH:11][C:10]([F:13])=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.[CH2:14]([NH2:18])[CH:15]([CH3:17])[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:13][C:10]1[CH:11]=[CH:12][C:2]([F:1])=[C:3]2[C:8]([N:18]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5](=[O:7])[C:4]=12)=[O:9]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 6558IsobutylamineHCID 5139183,6-Difluorophthalic anhydride

Produkt 1

HCID 220254173,6-difluoro-N-isobutylphthalimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3,6-Difluoro-N-isobutylphthalimide is prepared as described in Example 2, starting with 5.0 g of 3,6-difluorophthalic anhydride, 2.7 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 50 cm3 of toluene. The reaction mixture is refluxed for 3 hours. After cooling to a temperature in the region of 20° C., the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2 kPa). The residue is taken up in 50 cm3 of saturated aqueous sodium bicarbonate solution and washed 3 times with 80 cm3 of dichloromethane. The organic extracts are combined, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 6.41 g of 3,6-difluoro-N-isobutylphthalimide are thus obtained in the form of a pale yellow solid. (Rf=0.74, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

Aufarbeitung

  1. custom3,6-Difluoro-N-isobutylphthalimide is prepared
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated to dryness under reduced pressure (2 kPa)
  5. washwashed 3 times with 80 cm3 of dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-683685711d734bb8b0976c051a2d29bb
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589117B2

Notizen zur Reaktion

Wird geladen…