Hydrochloric Acid → N-ethyl-3-(4-amino-3-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 644863Notes

Reaction equation

HRID 644863 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)=[CH:16][C:15]=1[C:27]([F:30])([F:29])[F:28].Cl>C(OCC)(=O)C>[CH2:8]([NH:10][C:11]([N:23]1[C:24]([CH3:26])=[CH:25][C:21]([O:20][C:17]2[CH:18]=[CH:19][C:14]([NH2:13])=[C:15]([C:27]([F:28])([F:29])[F:30])[CH:16]=2)=[N:22]1)=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 178624003-(4-Amino-3-trifluoromethylphenyloxy)-5-methylpyrazole

Product 1

HCID 17862436N-ethyl-3-(4-amino-3-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamideYield 50.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.13 g, 1.3 mmol) and ethyl isocyanate (0.09 g, 1.3 mmol) were added to a solution of 3-(4-amino-3-trifluoromethylphenyloxy)-5-methylpyrazole (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 a yellowish solid of N-ethyl-3-(4-amino-3-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.19 g, yield: 50.5%). mp: 102-104° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.22 (t, J=7.3 Hz, 3H), 2.56 (d, J=0.8 Hz, 3H), 3.37 (dq, J=5.9 and 7.3 Hz, 2H), 4.11 (br s, 2H), 5.61 (q, J=0.8 Hz, 1H), 6.74 (d, J=8.8 Hz, 1H), 6.93 (br s, 1H), 7.14 (dd, J=2.7 and 8.8 Hz, 1H), 7.27 (d, J=2.7 Hz, 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-eb1832de616c420984cbf712fb313792
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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