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Hydrochloric Acid → HCID 17862437, Verbindung

HRID 644871
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 644871
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([N+:23]([O-:25])=[O:24])[C:14]=1[O:26][C:27]1[CH:31]=[C:30]([CH3:32])[NH:29][N:28]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:29]1[C:30]([CH3:32])=[CH:31][C:27]([O:26][C:14]2[C:15]([N+:23]([O-:25])=[O:24])=[CH:16][C:17]([C:19]([F:20])([F:21])[F:22])=[CH:18][C:13]=2[Cl:12])=[N:28]1)=[O:11])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 17862427HCID 17862427, Verbindung

Produkt 1

HCID 17862437HCID 17862437, VerbindungAusbeute 16,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

Potassium carbonate (0.30 g, 2.2 mmol) and ethyl isocyanate (0.14 g, 2.0 mmol) were added to a solution of 3-(2-chloro-6-nitro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.64 g, 2.0 mmol) in ethyl acetate (10 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 ethyl acetate (10 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=1/10), to give a yellowish solid of N-ethyl-3-(2-chloro-6-nitro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.13 g, yield: 16.6%). mp: 98-99° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.18 (t, J=7.2 Hz, 3H), 2.60 (d, J=0.5 Hz, 3H), 3.32 (dq, J=6.0 and 7.2 Hz, 2H), 5.87 (q, J=0.5 Hz, 1H), 6.40-6.65 (m, 1H), 8.01 (d, J=2.0 Hz, 1H), 8.17 (m, 1H).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 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=1/10)

Quellen und Nachweise

ORD-Eintrag
ord-a69a236f71b842758dc8cfddc03cf16f
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07700786B2

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