Reaktion #83375

Reaktionsgleichung

4-aminothiophenol

4-Aminothiophenol

sodium hydride

Water

2-Chloropyridine

→

2-(4-aminophenylthio)pyridine

Ausbeute 10.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenpreviously washed with hexane)
2. 2
   workup.STIRRINGthe reaction stirred at room temperature for 16 hr
3. 3
   Extraktionthe product extracted with ethyl acetate
4. 4
   WaschenThe solution was washed thoroughly with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe product was purified by HPLC over silica gel
8. 8
   Wascheneluted with 30% ethyl acetate/hexane

Vorschrift

4-Aminothiophenol (0.065 moles, 8.1 g) in 275 ml DMF was stirred at room temperature for 1 hr with sodium hydride (0.065 moles previously washed with hexane). 2-Chloropyridine (0.06 moles, 6.8 g) was added and the reaction mixture was stirred for 6 hr. An additional 5.2 g of 4-aminothiophenol was added and the reaction stirred at room temperature for 16 hr. Water was added and the product extracted with ethyl acetate. The solution was washed thoroughly with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)pyridine 1.2 g, 10%. Mass spec (FD) 202. Calculated for C11H10N2S: C, 65.32; H, 4.98, N, 13.85 Found: C, 65.23; H, 5.09; N, 13.63.

Quelle