Hydrochloric Acid → HCID 17862437, compound

HRID 644871Notes

Reaction equation

HRID 644871 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]([N+:23]([O-:25])=[O:24])[C:14]=1[O:26][C:27]1[CH:31]=[C:30]([CH3:32])[NH:29][N:28]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:29]1[C:30]([CH3:32])=[CH:31][C:27]([O:26][C:14]2[C:15]([N+:23]([O-:25])=[O:24])=[CH:16][C:17]([C:19]([F:20])([F:21])[F:22])=[CH:18][C:13]=2[Cl:12])=[N:28]1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 17862427HCID 17862427, compound

Product 1

HCID 17862437HCID 17862437, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.30 g, 2.2 mmol) and ethyl isocyanate (0.14 g, 2.0 mmol) were added to a solution of 3-(2-chloro-6-nitro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.64 g, 2.0 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature overnight. 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 yellowish solid of N-ethyl-3-(2-chloro-6-nitro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.13 g, yield: 16.6%). mp: 98-99° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.18 (t, J=7.2 Hz, 3H), 2.60 (d, J=0.5 Hz, 3H), 3.32 (dq, J=6.0 and 7.2 Hz, 2H), 5.87 (q, J=0.5 Hz, 1H), 6.40-6.65 (m, 1H), 8.01 (d, J=2.0 Hz, 1H), 8.17 (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-a69a236f71b842758dc8cfddc03cf16f
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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