Potassium Carbonate → HCID 21464836, compound

HRID 1939861Notes

Reaction equation

HRID 1939861 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:19]1[CH:20]=[C:21]([CH3:28])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26]>CS(C)=O>[CH3:28][C:21]1[CH:20]=[CH:19][C:24]([N+:25]([O-:27])=[O:26])=[C:23]([O:1][C:2]2[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 178481859HCID 178481859, compound

Product 1

HCID 21464836HCID 21464836, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

5-Hydroxy-1-methyl-3-trifluoromethylpyrazole (8.30 g, 50 mmol) and powdered potassium carbonate (8.29 g, 60 mmol) were stirred together in dimethylsulfoxide (40 ml) for 30 minutes. 3-Fluoro-4-nitrotoluene (7.76 g, 50 mmol) was added and the mixture heated at 70° C. for 17 h, then cooled to room temperature. 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, and the desired fraction collected and triturated with hexane to give the desired product as a pale yellow solid (6.20 g), m.p. 88°-90° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe mixture was partitioned between diethyl ether and water
  3. extractionthe ethereal extract
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated
  8. customThe residue was further purified by flash column chromatography over silica gel
  9. customthe desired fraction collected
  10. customtriturated with hexane

Sources & evidence

ORD record
ord-fa161f156d844fbc9d42a98d4350bc52
Source dataset
uspto-grants-1997_12
Patent number
US05698495

Reaction notes

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