Hydrochloric Acid → HCID 17862373, compound

HRID 644831Notes

Reaction equation

HRID 644831 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:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].Cl>CN(C=O)C>[CH3:13][C:11]1[NH:10][N:9]=[C:8]([O:7][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][C:16]=2[N+:25]([O-:27])=[O:26])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 17862373HCID 17862373, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (9.12 g, 66.0 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (5.88 g, 60.0 mmol) and 4-fluoro-3-nitrobenzotrifluoride (12.6 g, 60.0 mmol) in DMF (120 ml), and the mixture was stirred at 50° C. for 4 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (200 ml) and extracted with ethyl acetate (70 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 yellow solid of 5-methyl-3-(2-nitro-4-trifluoromethylphenyloxy)pyrazole (12.1 g, yield: 69.0%). mp: 89-91° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.28 (s, 3H), 5.77 (s, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.76 (dd, J=2.0 and 8.8 Hz, 1H), 8.21 (d, J=2.0 Hz, 1H), 10.10-11.05 (br s, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (70 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-7c01960f2b6e426e8223443687ce823b
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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