Phthalic Anhydride → HCID 69272449, Verbindung

HRID 2221108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221108
[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:19])=[CH:8][CH:7]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 6811Phthalic AnhydrideHCID 12731941ethyl N-(4-aminophenyl)carbamate

Produkt 1

HCID 69272449HCID 69272449, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(4-Amino-phenyl)-carbamic acid ethyl ester (118 g, 0.65 mol) is dissolved in glacial acetic acid (2.0 L) under nitrogen and the mixture is heated to 90° C. Phthalic anhydride (102.0 g, 0.69 mol) is added portionwise over 30 minutes and the reaction is kept at 90° C. for 2 hours. The mixture is allowed to cool to ambient temperature and the precipitated solid is filtered off. The solid is washed on the filter with water (2 L) followed by diethylether (3 L) and then dried in vacuo. Yield 127 g (62%) title compound as white crystalline compound. LC/MS (m/z) 311.3 (MH+); tR=2.57 min. 1H NMR (DMSO-d6): 1.26 (t, 3H); 4.15 (q, 2H); 7.34 (dd, 2H); 7.58 (dd, 2H); 7.90 (ddd, 2H); 7.95 (ddd, 2H); 9.80 (s, 1H, NH).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationthe precipitated solid is filtered off
  3. washThe solid is washed on the
  4. filtrationfilter with water (2 L)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a27cad8c7661460484fe27a5301cbc38
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368472B2

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