Hydrochloric Acid → N-methyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carbothioamide

HRID 644898Notes

Reaction equation

HRID 644898 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]=[C:9]=[S:10].[Cl:11][C:12]1[C:13]([O:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.Cl>CN(C=O)C>[CH3:7][NH:8][C:9]([N:25]1[C:26]([CH3:28])=[CH:27][C:23]([O:22][C:13]2[C:12]([Cl:11])=[CH:17][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:15][N:14]=2)=[N:24]1)=[S:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 11430Potassium CarbonateHCID 178624573-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole

Product 1

HCID 17862434N-methyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carbothioamideYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.75 g, 5.4 mmol) and methyl isothiocyanate (0.39 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 DMF (10 ml), and the mixture was stirred at room temperature for 8 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-methyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carbothioamide (0.35 g, yield: 37.7%) mp: 63-65° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.87 (d, J=0.6 Hz, 3H), 3.21 (d, J=4.9 Hz, 3H), 6.14 (q, J=0.6 Hz, 1H), 8.02 (d, J=2.1 Hz, 1H), 8.36 (m, 1H), 8.80-9.05 (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-e4af87f76c7c442aa11382028b5ceafe
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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