Acetic Acid → 3-(1-Methyl-1H-pyrazol-5-yl)-5-[4-(trifluoromethyl)phenyl]-1,2-oxazole

HRID 238379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238379
Cl.C(O)(=O)C.[OH:6][N:7]=[C:8]([C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1)[C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:26][N:25]1[C:21]([C:8]2[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=3)[O:6][N:7]=2)=[CH:22][CH:23]=[N:24]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136387777N-hydroxy-1-(1-methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-imine

Produkt 1

HCID 866848773-(1-Methyl-1H-pyrazol-5-yl)-5-[4-(trifluoromethyl)phenyl]-1,2-oxazoleAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Concentrated hydrochloric acid (0.50 mL) was added to an acetic acid (5.0 mL) solution of N-hydroxy-1-(1-methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-imine (303 mg) at a room temperature, and the obtained solution was then heated to reflux for 30 minutes. Thereafter, water was added to the reaction solution, and the obtained solution was then neutralized with potassium carbonate, followed by extraction with chloroform. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=3:2), so as to obtain the title compound (229 mg) in the form of a colorless solid.

Aufarbeitung

  1. temperaturethe obtained solution was then heated
  2. temperatureto reflux for 30 minutes
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with a saturated saline
  5. dry with materialwas then dried over anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=3:2)

Quellen und Nachweise

ORD-Eintrag
ord-56cc3c9dbc9a49ed903e6ca59232dc17
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642626B2

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