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Water → ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257417
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1257417
[NH2:1]/[C:2](=[N:14]\[OH:15])/[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=O.O>N1C=CC=CC=1>[F:16][C:17]([F:27])([F:28])[C:18]1[CH:19]=[C:20]([C:21]2[O:15][N:14]=[C:2]([CH2:3][N:4]3[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]3)[N:1]=2)[CH:24]=[CH:25][CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 58127695ethyl 1-[(2Z)-2-amino-2-hydroxyiminoethyl]pyrazole-4-carboxylate

Produkt 1

HCID 66939395ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylateAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A solution of the compound (2.2 g) obtained in Example 114a in pyridine (40 mL) was cooled in an ice bath and 3-(trifluoromethyl)benzoyl chloride (4.16 g) was added. The reaction mixture was heated to 110-120° C. overnight, cooled to room temperature, and poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was separated, washed successively with 1N aqueous hydrochloric acid solution, and saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-petroleum ether) to give the title compound (0.85 g) as a colorless solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed successively with 1N aqueous hydrochloric acid solution, and saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-6e47c27f1a0e4e3699b0f8edf3979550
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08461348B2

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