Hydrochloric Acid → HCID 17862361, compound

HRID 644886Notes

Reaction equation

HRID 644886 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[O:24][C:25]1[CH:29]=[C:28]([CH2:30][CH3:31])[NH:27][N:26]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:27]1[C:28]([CH2:30][CH3:31])=[CH:29][C:25]([O:24][C:14]2[C:15]([Cl:23])=[CH:16][C:17]([C:19]([F:22])([F:20])[F:21])=[CH:18][C:13]=2[Cl:12])=[N:26]1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 59263975HCID 59263975, compound

Product 1

HCID 17862361HCID 17862361, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.46 g, 3.3 mmol) and ethyl isocyanate (0.21 g, 3.0 mmol) were added to a solution of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-ethylpyrazole (0.98 g, 3.0 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 6 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 white solid of N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-ethylpyrazole-1-carboxamide (0.79 g, yield: 66.5%). mp: 86-89° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.19 (t, J=7.3 Hz, 3H), 1.27 (t, J=7.5 Hz, 3H), 3.06 (q, J=7.5 Hz, 2H), 3.34 (dq, J=6.1 and 7.3 Hz, 2H), 5.75 (s, 1H), 6.60-6.85 (m, 1H), 7.68 (s, 2H).

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-6a782be0760f402a968b407d5e99f22f
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

Loading…