Hydrochloric Acid → HCID 17862369, compound

HRID 644891Notes

Reaction equation

HRID 644891 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8].[Cl:12][C:13]1[C:14]([O:23][C:24]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[NH:26][N:25]=2)=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:26]1[C:27]([C:29]([F:32])([F:31])[F:30])=[CH:28][C:24]([O:23][C:14]2[C:13]([Cl:12])=[CH:18][C:17]([C:19]([F:22])([F:21])[F:20])=[CH:16][N:15]=2)=[N:25]1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 17862453HCID 17862453, compound

Product 1

HCID 17862369HCID 17862369, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.69 g, 5.0 mmol) and ethyl isocyanate (0.28 g, 5.0 mmol) were added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-trifluoromethylpyrazole (1.66 g, 5.0 mmol) in ethyl acetate (20 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 (20 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=1/5→1/1), to give a white solid of N-ethyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-trifluoromethylpyrazole-1-carboxamide (0.83 g, yield: 51.6%). mp: 52-54° C./1H-NMR (CDCl3, TMS, ppm): δ 1.34 (t, J=7.1 Hz, 3H), 3.75-4.30 (m, 2H), 5.66 (s, 1H), 7.98 (d, J=1.5 Hz, 1H), 8.64 (m, 1H), 10.20-10.40 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (20 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=1/5→1/1)

Sources & evidence

ORD record
ord-f29d682eaf8a49bdbaa6bff9feba6e76
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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