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1H-1,2,4-Triazole → Simeconazole

HRID 1464598
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464598
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[CH2:9][C:10]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([OH:16])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13]>CN(C)C=O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:10]([OH:16])([CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:9][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:22][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 12097219HCID 12097219, Verbindung

Produkt 1

HCID 10085783SimeconazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1.62 g (0.04 mole) of a 60% w/v dispersion of sodium hydride in mineral oil were added to 60 ml of dimethylformamide. Whilst the mixture was being stirred in an ice bath, 2.91 g (0.04 mole) of 1,2,4-triazole were added, and the mixture was stirred for a further 30 minutes at room temperature. At the end of this time, 5.5 g (0.021 mole) of 1 chloro-2-(4-fluorophenyl)-3-trimethylsilyl-2-propanol (prepared as described in Example 40) were added to the reaction mixture, which was then heated for 30 minutes at 90° C. whilst stirring. The reaction mixture was cooled and then poured into 200 ml of ice-water, and the resulting mixture was extracted with 300 ml of ethyl acetate. The organic extract was washed three times, each time with 100 ml of a saturated aqueous solution of sodium chloride. It was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to afford a crude oily product. 2.9 g (yield 47%) of the title compound, melting at 118 119° C., were obtained by purification of this crude oily product by silica gel column chromatography, using mixtures of ethyl acetate and hexane in proportions of 1:5, 1:1 and 2:1 as the eluent.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 30 minutes at room temperature
  2. stirringwhilst stirring
  3. temperatureThe reaction mixture was cooled
  4. extractionthe resulting mixture was extracted with 300 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed three times
  7. dry with materialIt was then dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customto afford a crude oily product

Quellen und Nachweise

ORD-Eintrag
ord-6f928412aafa4c20ab727b661f4c50b8
Quelldatensatz
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05306712

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