Ethylenediamine → 3-(1H-imidazol-2-yl)-2-methylpyridine

HRID 2068962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068962
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:10](N)[CH2:11][NH2:12].[S].[Mn]([O-])(=O)(=O)=O.[K+].[Si](=O)=O>C(O)C.C(#N)C.O.C1(C)C=CC=CC=1>[NH:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

9

Edukt 4

HCID 3301EthylenediamineHCID 47383082-Methylpyridine-3-carbonitrileHCID 5362487SulfurHCID 23697328Potassium permanganate silicon dioxide

Produkt 1

HCID 591988423-(1H-imidazol-2-yl)-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Methyl-3-pyridinecarbonitrile 1.05 g, ethylenediamine 5 mL and sulfur 71 mg were mixed, and stirred at 120° C. for 24 hours. Cooling it off to room temperature, toluene and water were added to effect phase separation. The aqueous layer was dried to solid under reduced pressure. Thus obtained crude product was mixed with potassium permanganate/silicon dioxide (carried at a ratio of 2.81 g:3.57 g) 6.38 g and acetonitrile 10 mL at room temperature, and stirred (inducing a rapid exothermic reaction). After the exotherm subsided and the reaction liquid was restored to room temperature, the liquid was diluted with 20 mL of ethanol and filtered through Celite. The solvent was distilled off and the residue was recrystallized from ethyl acetate/methanol (10:1) to provide 1.03 g of the title compound.

Aufarbeitung

  1. additionwere added to effect phase separation
  2. customThe aqueous layer was dried to solid under reduced pressure
  3. customThus obtained crude product
  4. customa rapid exothermic reaction)
  5. customthe reaction liquid
  6. customwas restored to room temperature
  7. filtrationfiltered through Celite
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized from ethyl acetate/methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-9d1c847ac47b42248fc7ec0677066b51
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299080B2

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