Hydrochloric Acid → N-methyl-5-ethyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamide

HRID 644885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644885
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]=[C:9]=[O:10].[CH2:11]([C:13]1[NH:17][N:16]=[C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=2[C:28]([F:31])([F:30])[F:29])[CH:14]=1)[CH3:12].Cl>C(OCC)(=O)C>[CH3:7][NH:8][C:9]([N:17]1[C:13]([CH2:11][CH3:12])=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=2[C:28]([F:29])([F:30])[F:31])=[N:16]1)=[O:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 178624155-Ethyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole

Produkt 1

HCID 17862465N-methyl-5-ethyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamideAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium carbonate (0.83 g, 6.0 mmol) and methyl isocyanate (0.29 g, 5.0 mmol) were added to a solution of 5-ethyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole (1.81 g, 6.0 mmol) in ethyl acetate (15 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 diethyl ether (20 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=1/7), to give a yellow solid of N-methyl-5-ethyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamide (1.42 g, yield: 79.3%). mp: 97-100° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.30 (t, J=7.5 Hz, 3H), 2.95 (d, J=5.0 Hz, 3H), 3.12 (q, J=7.5H, 2H), 5.93 (s, 1H), 6.75-7.00 (m, 1H), 7.45 (d, J=9.2 Hz, 1H), 8.41 (dd, J=2.7 and 9.2 Hz, 1H), 8.60 (d, J=2.7 Hz, 1H).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with diethyl ether (20 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=1/7)

Quellen und Nachweise

ORD-Eintrag
ord-ca16e2a769a243e68c5f6464c18e3401
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700786B2

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