Water → HCID 58542579, compound

HRID 1843087Notes

Reaction equation

HRID 1843087 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1.[F:12][C:13]([F:27])([F:26])[CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][N:4]1[C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:6][C:2]([O:1][CH2:14][C:13]([F:27])([F:26])[F:12])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 178498598HCID 178498598, compound

Product 1

HCID 58542579HCID 58542579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 200 mg (1.28 mmol) of methyl 3-hydroxy-1-methyl-5-pyrazolecarboxylate (for preparation see above) in 10 ml of N,N-dimethylformamide is admixed with 254 mg (2.56 mmol) of 2,2,2-trifluoroethyl-4-methylbenzenesulphonate and 138 mg (2.56 mmol) of potassium carbonate and the reaction mixture is heated at 100° C. for five hours and afterstirred at room temperature for two days. The reaction mixture is added to water and extracted several times with ethyl acetate. The organic phase is dried over sodium sulphate, filtered and concentrated by evaporation in vacuo on a rotary evaporator. This gives 500 mg of methyl 1-methyl-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carboxylate (50% strength, 82%).

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation in vacuo on a rotary evaporator

Sources & evidence

ORD record
ord-ef7f9e30e8b94d43be863a648f403a01
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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