Methyl iodide → 4-Bromo-1,3,5-trimethylpyrazole

HRID 975044Notes

Reaction equation

HRID 975044 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[CH3:7].[H-].[Na+].[H][H].IC.[C:15](=O)([O-])O.[Na+]>CN(C)C=O>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][N:5]([CH3:15])[C:6]=1[CH3:7]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 769374-bromo-3,5-dimethyl-1H-pyrazoleHCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, compound

Product 1

HCID 5191814-Bromo-1,3,5-trimethylpyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Bromo-3,5-dimethylpyrazole (10 g) in dry dimethylformamide (50 ml) was added to a stirred suspension of sodium hydride (1.8 g) in dry dimethylformamide at 0° C. When the evolution of hydrogen was complete, iodomethane (8.9 g) was added dropwise. The mixture was allowed to warm to room temperature and after 30 minutes saturated aqueous sodium hydrogen carbonate (5 ml) was added. Following evaporation under high vacuum, the residue was purified by column chromatography to give the title compound.

Workup

  1. additionwas added
  2. customevaporation under high vacuum
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e79adbce124645c4b6409d63aa4a694d
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Reaction notes

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