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p-Toluenesulfonic acid → HCID 22025506, Verbindung

HRID 733243
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 733243
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[O:11])[O:9][C:7](=O)[C:6]2=[CH:12][CH:13]=1.[CH2:16]([NH2:20])[CH:17]([CH3:19])[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:14][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]2[C:10](=[O:11])[N:20]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:7](=[O:9])[C:6]2=[CH:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 6558IsobutylamineHCID 127177895-(Trifluoromethyl)isobenzofuran-1,3-dione

Produkt 1

HCID 22025506HCID 22025506, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

4-Trifluoromethyl-N-isobutylphthalimide is prepared as described in Example 2, starting with 14.8 g of 4-trifluoromethylphthalic anhydride, 7.2 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 160 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 5 hours and is then cooled to a temperature in the region of 20° C. The reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. and the residue is taken up in 250 cm3 of ethyl acetate and 200 cm3 of saturated aqueous sodium hydrogen carbonate solution. The aqueous phase is separated out after settling has taken place and then extracted twice with 250 cm3 of ethyl acetate. The organic extracts are combined, washed with saturated brine, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 14.9 g of 4-trifluoromethyl-N-isobutylphthalimide are thus obtained in the form of a yellow powder (Rf=0.59, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

Aufarbeitung

  1. custom4-Trifluoromethyl-N-isobutylphthalimide is prepared
  2. temperatureis then cooled to a temperature in the region of 20° C
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C.
  4. customThe aqueous phase is separated out after settling
  5. extractionextracted twice with 250 cm3 of ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-f5c469ef839c406ea5a882a49c28524e
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07589117B2

Notizen zur Reaktion

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