反応 #51165

反応方程式

methanol

5-chloro-2-nitropyridine

methanol

sodium thiomethoxide

→

5-methylthio-2-nitropyridine

収率 45.3%

溶媒

water

反応条件

後処理

1. 1
   温度while being cooled with ice
2. 2
   workup.ADDITIONadded to the reaction mixture
3. 3
   抽出the mixture was extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with water
5. 5
   乾燥with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
6. 6
   workup.DISTILLATIONThereafter, the solvent was distilled off
7. 7
   その他the resulting crude product was recrystalized with ethyl acetate-hexane

実験手順

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.

出典