Sodium Methoxide → 4-Benzyl-3-bromo-5-methoxy-4H-1,2,4-triazole

HRID 1487985Notes

Reaction equation

HRID 1487985 reaction equation
[CH2:1]([N:8]1[C:12](Br)=[N:11][N:10]=[C:9]1[Br:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O-:16].[Na+]>CO>[CH2:1]([N:8]1[C:12]([O:16][CH3:15])=[N:11][N:10]=[C:9]1[Br:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 900291814-Benzyl-3,5-dibromo-4H-1,2,4-triazole2×

Product 1

HCID 900294944-Benzyl-3-bromo-5-methoxy-4H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-3,5-dibromo-4H-1,2,4-triazole (compound 91.2, 3.71 g, 11.7 mmol) in MeOH 15 mL) was added NaOMe (1.26 g, 23.4 mmol) and the mixture was refluxed for 18 hours. The mixture was cooled somewhat and additional NaOMe was added (1.26 g, 23.4 mmol). The mixture was refluxed for an additional 5 hours, then cooled to room temperature, and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with water (30 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to yield 3.13 g (theoretical) of the title compound as a clear oil. m/z (ES+) 269 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled somewhat
  3. temperatureThe mixture was refluxed for an additional 5 hours
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in EtOAc (200 mL)
  6. washwashed with water (30 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9629677f5d3e47e58313d0cc01e86d23
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…