Hydrochloric Acid → HCID 17862399, compound

HRID 644851Notes

Reaction equation

HRID 644851 reaction equation
C(N(CC)CC)C.[C:8]1([N:14]=[C:15]=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:17][C:18]1[NH:22][N:21]=[C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH:19]=1.Cl>C(OCC)(=O)C>[C:8]1([NH:14][C:15]([N:22]2[C:18]([CH3:17])=[CH:19][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:31])([F:32])[F:33])=[N:21]2)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 17862382HCID 17862382, compound

Product 1

HCID 17862399HCID 17862399, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.19 g, 1.4 mmol) and phenyl isocyanate (0.17 g, 1.4 mmol) were added to a solution of 5-methyl-3-(2-trifluoromethylphenyloxy)pyrazole (0.30 g, 1.2 mmol) in ethyl acetate (5 ml) at 0° C., and the mixture was allowed to have room temperature gradually and stirred for 6 hours. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (10 ml) and extracted with ethyl acetate (10 ml×2). An organic layer was washed with water (10 ml×2), 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=1/15), to give an orange solid of N-phenyl-5-methyl-3-(2-trifluoromethylphenyloxy)pyrazole-1-carboxamide (0.39 g, yield: 87.5%). mp: 87-89° C., 1H-NMR (CDCl3, TMS, ppm): δ 2.65 (d, J=0.7 Hz, 3H), 5.78 (d, J=0.7 Hz, 1H), 7.14 (ddd, J=1.2, 2.3 and 7.3 Hz, 1H), 7.28-7.38 (m, 4H), 7.51-7.60 (m, 3H), 7.69-7.73 (m, 1H), 8.90 (br s, 1H).

Workup

  1. customto have room temperature
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (10 ml×2)
  4. washAn organic layer was washed with water (10 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove a desiccant, and the solvent
  8. distillationwas distilled off from the filtrate under reduced pressure
  9. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/15)

Sources & evidence

ORD record
ord-95c0736be0204eab93685d78e2a2c7bc
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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