Hydrochloric Acid → N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 499995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499995
C(N(CC)CC)C.[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9].[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([F:24])[C:15]=1[O:25][C:26]1[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=1.Cl>C(OCC)(=O)C>[CH2:8]([NH:10][C:11]([N:28]1[C:29]([CH3:31])=[CH:30][C:26]([O:25][C:15]2[C:16]([F:24])=[CH:17][C:18]([C:20]([F:23])([F:21])[F:22])=[CH:19][C:14]=2[Cl:13])=[N:27]1)=[O:12])[CH3:9]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 178624283-(2-Chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole

Produkt 1

HCID 59422433N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamideAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triethylamine (2.02 g, 20.0 mmol) and ethyl isocyanate (1.42 g, 20.0 mmol) were added to an ethyl acetate (50 mL) solution of 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole (5.33 g, 18.0 mmol), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into 2 mol/L hydrochloric acid, followed by extraction with ethyl acetate (50 mL×3 times). The organic layer was washed with water and dried over anhydrous magnesium sulfate. Then, 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= 1/10) to give a white solid of N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (5.37 g, yield: 81.6%). Melting point: 84˜86° C., 1H-NMR (Acetone-d6, Acetone, ppm): δ1.10 (t, J=7.2 Hz, 3H), 2.55 (d, J=0.9 Hz, 3H), 3.26 (dq, J=6.1 and 7.2 Hz, 2H), 5.98 (q, J=0.9 Hz, 1H), 7.39˜7.48 (brt, J=6.1 Hz, 1H), 7.75 (ddq, J=2.1 and JHF=0.7 and 9.7 Hz, 1H), 7.82 (dq, 1H, J=2.1 and JHF=0.7 Hz).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate (50 mL×3 times)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThen, the desiccant was removed
  6. filtrationby filtering
  7. distillationthe solvent was distilled off the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane= 1/10)

Quellen und Nachweise

ORD-Eintrag
ord-0ee897b9984149399b28a6a980ea8808
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767827B2

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