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Dimethylformamide → HCID 54373171, Verbindung

HRID 1981511
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1981511
[H-].[Na+].[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1C1C=CC(=O)NC=1.[CH3:16][C:17]1C=CC(S(C)(=O)=O)=C[CH:22]=1.[CH3:27][N:28]([CH:30]=[O:31])[CH3:29]>>[CH3:27][N:28]1[CH:29]=[C:22]([N:3]2[CH:4]=[CH:5][N:6]=[CH:7][CH2:8]2)[CH:17]=[CH:16][C:30]1=[O:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 18521p-Tolyl methyl sulfoneHCID 24758Sodium hydrideHCID 233188115-(Pyrazin-2-yl)pyridin-2(1H)-one

Produkt 1

HCID 54373171HCID 54373171, Verbindung

Versuchsvorschrift

Sodium hydride (0.75 g) is added to a stirred solution of 5-(2-pyrazinyl)-2(1H) pyridone (2.2 g) in DMF (150 ml). Methyl p-toluene sulfonate (4.0 g) is added to the stirred reaction mixture after 5 minutes of stirring. After 35 minutes reaction time at RT, the reaction mixture is filtered and the filtrate evaporated in vacuum. The oily solid residue is washed with ether, filtered and the dry solid treated with hot acetone. The acetone is filtered and the filtrate evaporated, yielding a solid. The ether filtrate from above is evaporated, yielding a solid which after washing with decane is combined with the acetone filtrate solid. The combined solids are recrystallized from toluene and decane (treated with charcoal and filtered while hot) resulting in the desired 1-methyl pyridone compound, M.P. 165.5°-166.5° C.

Aufarbeitung

  1. customAfter 35 minutes reaction time at RT
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate evaporated in vacuum
  4. washThe oily solid residue is washed with ether
  5. filtrationfiltered
  6. additionthe dry solid treated with hot acetone
  7. filtrationThe acetone is filtered
  8. customthe filtrate evaporated
  9. customyielding a solid
  10. customThe ether filtrate from above is evaporated
  11. customyielding a solid which
  12. washafter washing with decane
  13. customThe combined solids are recrystallized from toluene and decane (treated with charcoal and filtered while hot)

Quellen und Nachweise

ORD-Eintrag
ord-eed850859f7a422893ebdc20948fa103
Quelldatensatz
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04593028

Notizen zur Reaktion

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