Hydrochloric Acid → N-isopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide

HRID 644875Notes

Reaction equation

HRID 644875 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([N:10]=[C:11]=[O:12])([CH3:9])[CH3:8].[Cl:13][C:14]1[C:15]([O:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.Cl>C(OCC)(=O)C>[CH:7]([NH:10][C:11]([N:27]1[C:28]([CH3:30])=[CH:29][C:25]([O:24][C:15]2[C:14]([Cl:13])=[CH:19][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:17][N:16]=2)=[N:26]1)=[O:12])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61277Isopropyl isocyanateHCID 178624573-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole

Product 1

HCID 17862469N-isopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamideYield 69.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.75 g, 5.4 mmol) and isopropyl isocyanate (0.46 g, 5.4 mmol) were added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole (1.00 g, 3.6 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (10 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=1/10), to give a colorless viscous substance of N-isopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.91 g, yield: 69.7%). 1H-NMR (CDCl3, TMS, ppm): δ 1.25 (d, J=6.5 Hz, 6H), 2.65 (d, J=0.8 Hz, 3H), 3.95-4.20 (m, 1H), 6.04 (q, J=0.8 Hz, 1H), 6.80˜7.00 (m, 1H), 8.02 (d, J=2.3 Hz, 1H), 8.35 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 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=1/10)

Sources & evidence

ORD record
ord-ccda02cc0d114058b441a9897c0a322c
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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