Reaktion #51165

Reaktionsgleichung

methanol

5-chloro-2-nitropyridine

methanol

sodium thiomethoxide

→

5-methylthio-2-nitropyridine

Ausbeute 45.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile being cooled with ice
2. 2
   workup.ADDITIONadded to the reaction mixture
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknenwith a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
6. 6
   workup.DISTILLATIONThereafter, the solvent was distilled off
7. 7
   Sonstigethe resulting crude product was recrystalized with ethyl acetate-hexane

Vorschrift

A methanol (40 mml) solution of 5-chloro-2-nitropyridine (2.0 g, 12.6 mmol) was added dropwise to a methanol (20 ml) solution of sodium thiomethoxide (1.02 g, 13.9 mmol) while being cooled with ice, and after the mixture was stirred for 13 hours while raising its temperature to the room temperature, water added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the resulting crude product was recrystalized with ethyl acetate-hexane to obtain 972 mg (yield 45%) of 5-methylthio-2-nitropyridine.

Quelle