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

HRID 644909Notes

Reaction equation

HRID 644909 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[Cl:9][C:10]1[C:11]([O:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH2:1]([N:3]([CH2:7][CH3:8])[C:4]([N:23]1[C:24]([CH3:26])=[CH:25][C:21]([O:20][C:11]2[C:10]([Cl:9])=[CH:15][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:13][N:12]=2)=[N:22]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 178624573-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole

Product 1

HCID 17862407N,N-diethyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamideYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Diethylcarbamoyl chloride (1.52 g, 7.8 mmol) was added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole (1.39 g, 5.0 mmol) and potassium carbonate (1.98 g, 14.3 mmol) in DMF (15 ml), the mixture was stirred at 70° C. for 9 hours and further stirred at room temperature for 2 days. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid, and the mixture was 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. 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), to give a colorless viscous substance of N,N-diethyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.21 g, yield: 11.2%). 1H-NMR (CDCl3, TMS, ppm): δ 1.21 (t, J=7.0 Hz, 6H), 2.48 (d, J=0.6 Hz, 3H), 3.47 (q, J=7.0 Hz, 4H), 6.00 (q, J=0.6 Hz, 1H), 7.99 (d, J=2.1 Hz, 1H), 8.33 (m, 1H).

Workup

  1. stirringfurther stirred at room temperature for 2 days
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate (20 ml×3)
  4. washAn organic-layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove a desiccant
  8. distillationThe solvent was distilled off from the filtrate under reduced pressure
  9. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-62d2720719624a72a2c7c9807bcf38dc
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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