Sodium Methoxide → 2-Methoxy-6-(1H-1,2,3-triazol-1-yl)pyridine

HRID 867629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867629
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)[N:3]=1.[CH3:13][O-:14].[Na+]>CS(C)=O>[CH3:13][O:14][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)[N:3]=1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 212903442-chloro-6-(1H-1,2,3-triazol-1-yl)pyridine

Produkt 1

HCID 212903472-Methoxy-6-(1H-1,2,3-triazol-1-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4.00 g (20 mmol) of 2-chloro-6-(1H-1,2,3-triazol-1-yl)pyridine and 8.5 ml of sodium methoxide (25 percent in methanol, 40 mmol) in dimethyl sulfoxide was heated at 80° C. for six hours. The mixture was cooled, poured over ice and extracted with methylene chloride. The extract was dried over magnesium sulfate and stripped of solvent. The solid residue was triturated in a minimal amount of methanol and filtered to yield 0.4 g (10 percent of theory) of tan solid product; m.p., 75°-78° C. NMR (CDCl3): δ8.60 (s, 1H); δ7.94 (m, 3H); δ6.90 (m, 1H); δ4.06 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. additionpoured over ice
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customThe solid residue was triturated in a minimal amount of methanol
  6. filtrationfiltered
  7. customto yield 0.4 g (10 percent of theory) of tan solid product
  8. customm.p., 75°-78° C

Quellen und Nachweise

ORD-Eintrag
ord-656df5e076854cab914dc117ff677bf1
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775762

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