반응 #44982

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Pyrazine-2-carbonitrile

sulfuryl chloride

→

title compound

수율 47.4%

3-Chloropyrazine-2-carbonitrile

수율 47.4%

용매

toluene

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.ADDITIONAfter completion of addition
3. 3
   기타The toluene layer is separated
4. 4
   추출the residual red oil is extracted with diethyl ether
5. 5
   온도cooled with ice
6. 6
   workup.ADDITIONafter pouring
7. 7
   workup.ADDITIONby adding saturated aqueous sodium hydrogen carbonate solution
8. 8
   기타The organic layer is separated
9. 9
   추출aqueous layer is extracted with diethyl ether
10. 10
    세척washed with water
11. 11
    건조dried over sodium sulfate
12. 12
    기타evaporated
13. 13
    기타to remove the solvent under reduced pressure
14. 14
    기타The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

실험 절차

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).

출처