Trimellitic anhydride → 2-(2-Morpholinoethyl)-1,3-dioxoisoindoline-5-carboxylic acid

HRID 252876

Reaktionsgleichung

Reaktionsgleichung von HRID 252876
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]2[C:10]([O:12][C:13](=[O:14])[C:3]=2[CH:2]=1)=O.[NH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)(=O)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][N:15]2[C:10](=[O:12])[C:4]3[C:3](=[CH:2][CH:1]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=3)[C:13]2=[O:14])[CH2:19][CH2:20]1

Komponenten

4

Edukt 2

HCID 11089Trimellitic anhydrideHCID 4082852-Morpholinoethylamine

Produkt 1

HCID 597368682-(2-Morpholinoethyl)-1,3-dioxoisoindoline-5-carboxylic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1,2,4-Benzenetricarboxylic anhydride (356, 0.487 g, 2.53 mmol) and 4-(2-aminoethyl)morpholine (0.33 g, 2.53 mmol) were allowed to stir 2 hours at 130° C. in acetic acid (10 mL). The reaction mixture was then cooled to room temperature and the precipitated solid was collected by filtration, washed with H2O and dried under vacuum, to afford title compound 357 as a white powder (0.63 g, 82% yield). 1H NMR (DMSO) δ (ppm): 8.26 (dd, J=7.6, 1.4 Hz, 1H), 8.15 (dd, J=1.4, 0.6 Hz, 1H), 7.92 (dd, J=7.6, 0.6 Hz, 1H), 3.73 (t, J=6.5 Hz, 2H), 3.50 (t, J=4.5 Hz, 4H), 2.59 (t, J=6.5 Hz, 2H), 2.47 (overlapped with DMSO, 4H). MS: 304.3 (calc), 305.1 (obs).

Aufarbeitung

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with H2O
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-45c99c82dd824e318b094a53657e5daa
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868205B2

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