反応 #44982

反応方程式

Pyrazine-2-carbonitrile

sulfuryl chloride

→

title compound

収率 47.4%

3-Chloropyrazine-2-carbonitrile

収率 47.4%

溶媒

toluene

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.ADDITIONAfter completion of addition
3. 3
   その他The toluene layer is separated
4. 4
   抽出the residual red oil is extracted with diethyl ether
5. 5
   温度cooled with ice
6. 6
   workup.ADDITIONafter pouring
7. 7
   workup.ADDITIONby adding saturated aqueous sodium hydrogen carbonate solution
8. 8
   その他The organic layer is separated
9. 9
   抽出aqueous layer is extracted with diethyl ether
10. 10
    洗浄washed with water
11. 11
    乾燥dried over sodium sulfate
12. 12
    その他evaporated
13. 13
    その他to remove the solvent under reduced pressure
14. 14
    その他The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

実験手順

Pyrazine-2-carbonitrile (26.36 g) is dissolved in toluene (187 ml)/N,N-dimethylformamide (19 ml), and thereto is added dropwise sulfuryl chloride (135 g) under ice-cooling. After completion of addition, the reaction solution is warmed to room temperature gradually and stirred overnight. The toluene layer is separated and the residual red oil is extracted with diethyl ether. The organic layers are combined, cooled with ice, and after pouring thereto ice-water, neutralized by adding saturated aqueous sodium hydrogen carbonate solution. The organic layer is separated, and aqueous layer is extracted with diethyl ether. The organic layers are combined, washed with water, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to give the title compound (16.58 g).

出典