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1H-1,2,4-Triazole → Simeconazole

HRID 1464599
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464599
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH2:17][O:16]2)=[CH:11][CH:10]=1>CC(N(C)C)=O>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([OH:16])([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH2:17][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 190867842-(4-Fluorophenyl)-2-trimethylsilylmethyloxirane

Produkt 1

HCID 10085783SimeconazoleAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

0.237 g (6.18 mmole) of a 60% w/v dispersion of sodium hydride in mineral oil was added to 10 ml of dimethylacetamide. The mixture was then cooled in an ice-water bath, after which 0.854 g (12.37 mmole) of 1,2,4-triazole was added, whilst stirring. The reaction mixture was stirred for 30 minutes, and then 1.4 g (6.24 mmole) of 2-(4-fluorophenyl)-2-trimethylsilylmethyloxirane (prepared as described in Example 66) were added. The mixture was stirred for a further 2 hours at 80° C., after which it was cooled, and the mixture was poured into 50 ml of ice water and extracted with 100 ml of ethyl acetate. The organic extract was washed twice, each time with 50 ml of a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to obtain crude crystals These crystals were recrystallized from diisopropyl ether, to give 1.01 g (yield 55%) of the title compound, as crystals, melting at 118°-119° C.

Aufarbeitung

  1. temperatureThe mixture was then cooled in an ice-water bath
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. stirringThe mixture was stirred for a further 2 hours at 80° C.
  4. temperatureafter which it was cooled
  5. extractionextracted with 100 ml of ethyl acetate
  6. extractionThe organic extract
  7. washwas washed twice
  8. dry with materialeach time with 50 ml of a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customto obtain crude crystals These crystals
  11. customwere recrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e63c4b7c1ec044c79704cf13be7d985a
Quelldatensatz
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05306712

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