Hydrochloric Acid → HCID 17862424, compound

HRID 644835Notes

Reaction equation

HRID 644835 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:12]=[C:11]([CH3:13])[NH:10][N:9]=1.F[C:15]1[CH:16]=[CH:17][C:18]([N+:25]([O-:27])=[O:26])=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.Cl>CN(C=O)C>[CH3:13][C:11]1[NH:10][N:9]=[C:8]([O:7][C:15]2[CH:16]=[CH:17][C:18]([N+:25]([O-:27])=[O:26])=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:20]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 17862424HCID 17862424, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (2.49 g, 18.0 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (1.47 g, 15.0 mmol) and 5-fluoro-2-nitrobenzotrifluoride (3.14 g, 15.0 mmol) in DMF (20 ml), and the mixture was stirred under heating at 70° C. for 3 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (40 ml) and extracted with ethyl acetate (30 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/3), to give a yellowish solid of 5-methyl-3-(4-nitro-3-trifluoromethylphenyloxy)pyrazole (2.74 g, yield: 63.6%). mp: 96-98° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.34 (s, 3H), 5.77 (s, 1H), 7.40 (dd, J=2.6 and 8.9 Hz, 1H), 7.56 (d, J=2.6 Hz, 1H), 7.98 (d, J=8.9 Hz, 1H), 9.20-10.15 (br s, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (30 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-ef9eca72aec74c08974f40e5fbef9f37
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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