Methyl iodide → 1-Methyl-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester

HRID 1024315Notes

Reaction equation

HRID 1024315 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[NH:7][N:6]=1)=[O:4].[C:14](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:13][O:12][C:10]([C:8]1[CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]([CH3:14])[N:7]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14844913,5-dimethyl 1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 125636171-Methyl-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1H-Pyrazole-3,5-dicarboxylic acid dimethyl ester (639, 9.1 g, 49.0 mmol) was combined with acetone (400 mL) and potassium carbonate (10.2 g, 74.1 mmol). The mixture was stirred for 40 minutes under an atmosphere of nitrogen. To the stirring suspension, methyl iodide (3.4 mL, 54.0 mmol) was added dropwise. The reaction was stirred at room temperature overnight and then the solvent was evaporated under reduced pressure. The resulting solid was washed with water and filtered. After toluene was added, the solvent was removed under reduced pressure. The resulting compound 640 was used without further purification.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customthe solvent was evaporated under reduced pressure
  3. washThe resulting solid was washed with water
  4. filtrationfiltered
  5. additionAfter toluene was added
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting compound 640 was used without further purification

Sources & evidence

ORD record
ord-9663f85e5bca40fd8b8368656d86dbf3
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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