Phthalic Anhydride → 2-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione

HRID 610465

Reaktionsgleichung

Reaktionsgleichung von HRID 610465
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18]>C1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>[C:4]1(=[O:6])[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Komponenten

5

Edukt 2

HCID 6811Phthalic AnhydrideHCID 13578Diglycolamine

Produkt 1

HCID 27554062-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dioneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A suspension of 30.0 g (202.5 mmol) of phthalic anhydride, 20 mL (21.0 g, 199.4 mmol) of 2-(2-aminoethoxy)-ethanol in 400 mL of benzene was added 1.0×10-2 g (5.3×10-5 mmol) of TsOH.H2O. The reaction flask was connected to a Dean-Stark condenser and then heated to reflux for 14 h. The solvent was removed at reduced pressure and the residue was purified by SiO2 column chromatography (hexanes/AcOEt 1:1 then CHCl3 /MeOH 20:1) gave 43.7 g (93.1%) of 13 as a light yellow syrup. This syrup slowly crystallized on standing at room temperature overnight as needle-like crystals. mp 66-66.5° C. Rf (hexanes/AcOEt 1:1) 0.17. 1H NMR (CDCl3) d 2.41 (t, 1H, J=6.2 Hz, OH), 3.57-3.93 (m, 8 H), 7.69-7.87 (m, 4H). 13C NMR (CDCl3) d 37.52, 61.62, 68.24, 72.24, 123.36, 131.97, 134.00, 168.38 (C=O). Anal Calcd for C12H13NO4 : C, 61.28; H, 5.53; N, 5.96. Found: C, 61.34; H, 5.62; N, 5.94.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 14 h
  3. customThe solvent was removed at reduced pressure
  4. customthe residue was purified by SiO2 column chromatography (hexanes/AcOEt 1:1

Quellen und Nachweise

ORD-Eintrag
ord-f0f3dc64ca53489397e1c5b33a56024e
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998603

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