Reaktion #83348

Reaktionsgleichung

4-Chloroquinoline

4-nitrothiophenol

potassium carbonate

→

4-(4-nitrophenylthio)quinoline

Ausbeute 54.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated
2. 2
   workup.ADDITIONethyl acetate was added
3. 3
   Waschenthe solution washed with water
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe product was purified by HPLC over silica gel
7. 7
   Wascheneluted with 20-40% ethyl acetate/hexane

Vorschrift

4-Chloroquinoline (32.3 mmoles, 5.2 g),4-nitrothiophenol (32.3 moles, 5.0 g) and potassium carbonate (32.3 moles, 4.46 g) were stirred at room temperature in 500 ml of ethanol for 16 hr. The reaction mixture was then concentrated, ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 20-40% ethyl acetate/hexane to yield 4-(4-nitrophenylthio)quinoline 4.9 g, 54%. Mass Spec (FD) 282. Calculated for C15H10N2O2S: C, 63.82 H, 3.57 N, 9.92. Found: C, 65.09; H, 3.81; N, 10.02.

Quelle