Water → Methyl 5-(difluoromethoxy)-1-methyl-1H-pyrazole-3-carboxylate

HRID 1653954Notes

Reaction equation

HRID 1653954 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([OH:10])[N:7]([CH3:11])[N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH:19]([F:21])[F:20].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([O:10][CH:19]([F:21])[F:20])[N:7]([CH3:11])[N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 178498595HCID 178498595, compound

Product 1

HCID 54319416Methyl 5-(difluoromethoxy)-1-methyl-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

67.6 g (0.43 mol) 3-Methoxycarbonyl-5-hydroxy-1-methylpyrazole and 299.2 g (2.17 mol) potassium carbonate were dissolved in 1500 ml dimethylformamide and warmed to 70° C. At this temperature, chlorodifluoromethane was passed through for 2 hours and then stirred for 1.5 hours at 80° C. The reaction mixture was added to water and shaken 6 times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride and dried over magnesium sulfate. The reaction solution was concentrated.

Workup

  1. customwas passed through for 2 hours
  2. washThe combined organic phases were washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-b06baf9de85b4fbd9eedd8b5ace774f5
Source dataset
uspto-grants-1995_04
Patent number
US05405829

Reaction notes

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