p-Toluenesulfonic acid monohydrate → HCID 15908403, Verbindung

HRID 396754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396754
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH:12]=[CH:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:29]=[CH:28][C:26]([N:27]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH3:15])=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 41911054-(2-Furyl)Aniline HydrochlorideHCID 54299304HCID 54299304, Verbindung

Produkt 1

HCID 15908403HCID 15908403, VerbindungAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-[4-(methylsulfonyl)phenyl]pentene-1 4-dione (0.305 g, 1.2 mmol prepared according to the method of J. Med. Chem., 1997, 40, 1619), 4-(2-furyl)aniline (0.35 g, 2 mmol), and p-toluenesulfonic acid monohydrate (0.015 g) in toluene (40 mL) was heated at reflux temperature for 16 hours using Dean-Stark apparatus. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (4/1). The resulting solid was recrystallized from CH2Cl2/hexane to give the title compound (0.11 g, 24.3% yield).

Aufarbeitung

  1. customprepared
  2. temperatureat reflux temperature for 16 hours
  3. temperatureAfter cooling
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane/ethyl acetate (4/1)
  7. customThe resulting solid was recrystallized from CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag
ord-91780cf7a27e46949551b12c5a53c5e7
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608095B2

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