Reaktion #50485

Reaktionsgleichung

sodium hydride

2-Nitromethylenethiazolidine

2-chloro-5-pyridylmethyl chloride

hydrogen

→

3-(2-chloro-5-pyridylmethyl)-2-nitromethylenethiazolidine

Ausbeute 29.8%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONAcetonitrile was then distilled off under reduced pressure, and dichloromethane
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   WaschenThe mixture was then washed with water
4. 4
   workup.DISTILLATIONDichloromethane was distilled off from the dichloromethane layer
5. 5
   SonstigeThe remaining oil was purified by silica gel column chromatography

Vorschrift

2-Nitromethylenethiazolidine (2.9 g) was dissolved in dry acetonitrile (30 ml), and 60% sodium hydride (0.9 g) was added at room temperature in a stream of nitrogen. Subsequently, the mixture was stirred at room temperature until the generation of hydrogen ceased. Then, a solution of 2-chloro-5-pyridylmethyl chloride (3.2 g) in dry acetonitrile (5 ml) was added at room temperature, and the mixture was stirred at room temperature for 1 day. Acetonitrile was then distilled off under reduced pressure, and dichloromethane was added to the residue. The mixture was then washed with water. Dichloromethane was distilled off from the dichloromethane layer. The remaining oil was purified by silica gel column chromatography to give the desired 3-(2-chloro-5-pyridylmethyl)-2-nitromethylenethiazolidine (1.6 g).

Quelle