Hydrochloric Acid → HCID 17862470, compound

HRID 644865Notes

Reaction equation

HRID 644865 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:10]=[C:11]=[O:12])[CH2:8][CH3:9].[CH3:13][C:14]1[NH:18][N:17]=[C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([C:29]([F:32])([F:31])[F:30])[CH:21]=2)[CH:15]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:10][C:11]([N:18]1[C:14]([CH3:13])=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([C:29]([F:30])([F:31])[F:32])[CH:21]=2)=[N:17]1)=[O:12])[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61033Propyl isocyanateHCID 17862424HCID 17862424, compound

Product 1

HCID 17862470HCID 17862470, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.30 g, 2.2 mmol) and propyl isocyanate (0.17 g, 2.0 mmol) were added to a solution of 5-methyl-3-(4-nitro-3-trifluoromethylphenyloxy)pyrazole (0.57 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 yellow viscous substance of N-propyl-5-methyl-3-(4-nitro-3-trifluoromethylphenyloxy)pyrazole-1-carboxamide (0.64 g, yield: 69.0%). 1H-NMR (CDCl3, TMS, ppm): δ 0.97 (t, J=7.3 Hz, 3H), 1.62 (q, J=7.3 Hz, 2H), 2.64 (s, 3H), 3.32 (dt, J=7.3 and 7.3 Hz, 2H), 5.85 (m, 1H), 6.80˜7.05 (m, 1H), 7.45 (dd, J=2.6 and 9.0 Hz, 1H), 7.64 (d, J=2.6 Hz, 1H), 8.00 (d, J=9.0 Hz, 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-979887cadc9940029fad5999d4ce3ec1
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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