Potassium Carbonate → HCID 67659168, compound

HRID 1957474Notes

Reaction equation

HRID 1957474 reaction equation
[OH:1][C:2]1[N:6](C)[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].F[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27]>CS(C)=O>[F:25][C:23]1[CH:24]=[CH:19][C:20]([N+:26]([O-:28])=[O:27])=[C:21]([O:1][C:2]2[NH:6][N:5]([CH3:12])[CH:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 178481859HCID 178481859, compound

Product 1

HCID 67659168HCID 67659168, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Hydroxy-1-methyl-3-trifluoromethylpyrazole (8.3 g, 50 mmol) and powdered potassium carbonate (8.3 g, 60 mmol) were stirred together in dimethylsulfoxide (40 ml) for 30 minutes. 2,4-Difluoronitrobenzene (7.9 g, 50 mmol) was added and the mixture stirred at room temperature for 18 h. The mixture was partitioned between diethyl ether and water, the ethereal extract washed with water and brine, dried over magnesium sulfate, filtered and the filtrate evaporated. The residue was further purified by flash column chromatography over silica gel, to give the desired product (2.3 g) as a solid. m.p. 68°-70° C.

Workup

  1. customThe mixture was partitioned between diethyl ether and water
  2. extractionthe ethereal extract
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customThe residue was further purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-4d546244fa2c4a92bf4f7354eddfa32d
Source dataset
uspto-grants-1998_07
Patent number
US05786302

Reaction notes

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