Hydrochloric Acid → HCID 17862385, compound

HRID 644908Notes

Reaction equation

HRID 644908 reaction equation
[OH-:1].[K+].OO.[CH2:5]([NH:9][C:10]([N:12]1[C:16]([CH3:17])=[CH:15][C:14]([O:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=2)=[N:13]1)=S)[CH2:6][CH2:7][CH3:8].Cl>CO>[CH2:5]([NH:9][C:10]([N:12]1[C:16]([CH3:17])=[CH:15][C:14]([O:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=2)=[N:13]1)=[O:1])[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 17862329HCID 17862329, compound

Product 1

HCID 17862385HCID 17862385, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (0.42 g, 7.5 mmol) and 30% hydrogen peroxide (2.7 ml) were added to a solution of N-butyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carbothioamide (0.98 g, 2.5 mmol) in methanol (10 ml), and the mixture was stirred at room temperature for 3 hours. Concentrated hydrochloric acid was added to the reaction mixture up to a pH of 1, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (15 ml×3), and the 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=1/10→1/1), to give a colorless viscous substance of N-butyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.17 g, yield: 18.1%). 1H-NMR (CDCl3, TMS, ppm): δ 0.94 (t, J=7.3 Hz, 3H), 1.30-1.50 (m, 2H), 1.50-1.70 (m, 2H), 2.65 (s, 3H), 3.35 (dt, J=6.3 and 6.3 Hz, 2H), 6.04 (s, 1H), 6.90-7.20 (m, 1H), 8.02 (d, J=2.0 Hz, 1H), 8.35 (m, 1H).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate (15 ml×3)
  4. washthe 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=1/10→1/1)

Sources & evidence

ORD record
ord-2d2dad8003e347cba1c277e5ee97aa5c
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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