Cyclopropanecarbonyl chloride → N-(Pyrazin-2-YL)cyclopropanecarboxamide

HRID 133073

Reaktionsgleichung

Reaktionsgleichung von HRID 133073
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1>N1C=CC=CC=1.ClCCl>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[NH:1][C:11]([CH:8]1[CH2:10][CH2:9]1)=[O:12]

Komponenten

5

Edukt 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 78747Aminopyrazine

Produkt 1

HCID 4047267N-(Pyrazin-2-YL)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 10 g (105 mmol) of 2-aminopyrazine in 100 mL of pyridine was added dropwise a solution of 10.99 g (9.56 mL, 105 mmol) of cyclopropanecarbonyl chloride in 100 mL of dichloromethane. The resultant yellow solution was stirred at ambient temperature for 2 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and a small amount of water and washed sequentially with 1 M aqueous cuprous sulfate solution and water. The water layer was extracted with three portions of ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, and concentrated. Purification by flash chromatography (silica gel, eluting sequentially with 50%, 80% and 100% ethyl acetate/hexane) gave the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washa small amount of water and washed sequentially with 1 M aqueous cuprous sulfate solution and water
  4. extractionThe water layer was extracted with three portions of ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel
  9. washeluting sequentially with 50%, 80% and 100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5b9846e3a40944a59e65c0cb56916691
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390809B2

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