Pyridine → 4-Chloro-N-phenylphthalimide

HRID 1379904

Reaktionsgleichung

Reaktionsgleichung von HRID 1379904
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.C(OC(=O)C)(=O)C>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6](=[O:8])[C:5]2=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6115AnilineHCID 7918Acetic AnhydrideHCID 670444-Chlorophthalic anhydride

Produkt 1

HCID 111187184-Chloro-N-phenylphthalimideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 4-chlorophthalic anhydride (9.12 g, 500 mmol), aniline (4.65 g, 50 mmol), pyridine (12.01 g, 152 mmol) and DMAc (40 mL) was heated at 70° C. for 1 hour under argon. Acetic anhydride (20.0 g, 196 mmol) was added and the solution was allowed to stir at 80° C. for a total of 4 hours. The reaction mixture was cooled to ca. 5° C. and the crystalline solid removed by filtration, washed with acetone and methanol and dried in vacuo to give 9.0 g (70%) product which was recrystallized from acetic anhydride, mp 187°-189° C., (liturature melting point) 189.5°-191° C. 1H NMR(CDCl3) δ7.90 (d, J=1.6 Hz, 1), 7.88 (d, J=8.0 Hz, 1), 7.73 (dd, J=8.0, 1.6 Hz, 1), 7.50 (m, 2), 7.41 (m,3). 13C NMR (CDCl3) {1H} δ166.2, 165.9 141.1, 134.4, 133.5, 131.5, 129.9, 129.1, 128.2, 126.4, 124.9, 124.1.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ca. 5° C.
  2. customthe crystalline solid removed by filtration
  3. washwashed with acetone and methanol
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a5020b6742ea46d3825e1c94eff75541
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672750

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