Triethylamine → N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 499998Notes

Reaction equation

HRID 499998 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([Cl:20])[C:11]=1[O:21][C:22]1[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=1.[CH2:28]([NH2:34])[CH:29]1[O:33][CH2:32][CH2:31][CH2:30]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:28]([NH:34][C:2]([N:24]1[C:25]([CH3:27])=[CH:26][C:22]([O:21][C:11]2[C:10]([Cl:9])=[CH:15][C:14]([C:16]([F:19])([F:17])[F:18])=[CH:13][C:12]=2[Cl:20])=[N:23]1)=[O:3])[CH:29]1[O:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 253298TetrahydrofurfurylamineHCID 178623603-(2,6-Dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

Product 1

HCID 57548574N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamideYield 28.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trichloromethyl chloroformate (0.49 g, 2.5 mmol) was added to a chloroform (10 mL) solution of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.78 g, 2.5 mmol) at 0° C., and while the mixture was allowed to gradually warm up to a room temperature, it was further stirred at room temperature for 3 hours. Tetrahydrofurfurylamine (0.51 g, 5.0 mmol) and triethylamine (1.01 g, 10 mmol) were added to the reaction mixture, and the mixture was refluxed under heating for 4 hours. After completion of the reaction, the reaction mixture was poured into ice and extracted with chloroform (20 mL×3 times). The organic layer was washed with water and dried over anhydrous magnesium sulfate, the desiccant was removed by filtering, and the solvent was distilled off the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate:hexane=1:7) to give a white solid of N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.31 g, yield: 28.3%). Melting point: 74˜76° C., 1H-NMR (CDCl3, TMS, ppm): δ1.45˜1.65 (m, 1H), 1.75-2.05 (m, 3H), 2.58 (d, J=0.8 Hz, 3H), 3.32 (dt, J=6.2 and 13.9 Hz, 1H), 3.47 (ddd, J=3.7, 5.6 and 13.9 Hz, 1H), 3.60˜3.85 (m, 2H), 3.95˜4.15 (m, 1H), 5.75 (q, J=0.8 Hz, 1H), 6.85˜7.15 (m, 1H), 7.66 (s, 2H).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was poured into ice
  5. extractionextracted with chloroform (20 mL×3 times)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe desiccant was removed
  9. filtrationby filtering
  10. distillationthe solvent was distilled off the filtrate under reduced pressure
  11. customThe resultant crude product was purified with a silica gel column (ethyl acetate:hexane=1:7)

Sources & evidence

ORD record
ord-2f2b8c4fdf66471693653b2fda67208f
Source dataset
uspto-grants-2010_08
Patent number
US07767827B2

Reaction notes

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