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

HRID 867629Notes

Reaction equation

HRID 867629 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-656df5e076854cab914dc117ff677bf1
Source dataset
uspto-grants-1988_10
Patent number
US04775762

Reaction notes

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