Sulfuryl chloride → 3-Chloropyrazine-2-carbonitrile

HRID 16704

Reaktionsgleichung

Reaktionsgleichung von HRID 16704
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[N:8].S(Cl)([Cl:12])(=O)=O>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:12][C:3]1[C:2]([C:7]#[N:8])=[N:1][CH:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 2

HCID 24648Sulfuryl chlorideHCID 73172Pyrazinecarbonitrile

Produkt 1

HCID 2924653-Chloropyrazine-2-carbonitrileAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturecooling
  2. additionAfter completion of addition
  3. customThe toluene layer is separated
  4. extractionthe residual red oil is extracted with diethyl ether
  5. temperaturecooled with ice
  6. additionafter pouring
  7. additionby adding saturated aqueous sodium hydrogen carbonate solution
  8. customThe organic layer is separated
  9. extractionaqueous layer is extracted with diethyl ether
  10. washwashed with water
  11. dry with materialdried over sodium sulfate
  12. customevaporated
  13. customto remove the solvent under reduced pressure
  14. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-0130e7830dff4585b90743179ee76437
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737161B2

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