Sodium hydride → 2-[3-(4-Cyanostyryl)-1,2,4-triazol-1-yl]-1-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl methyl)ethanol

HRID 1650796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650796
[H-].[Na+].[C:3]([C:5]1[CH:17]=[CH:16][C:8]([CH:9]=[CH:10][C:11]2[N:15]=[CH:14][NH:13][N:12]=2)=[CH:7][CH:6]=1)#[N:4].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]1([O:34][CH2:33]1)[CH2:27][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CN(C)C=O.O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[CH:10][C:11]2[N:15]=[CH:14][N:13]([CH2:33][C:26]([C:20]3[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=3[F:18])([CH2:27][N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)[OH:34])[N:12]=2)=[CH:16][CH:17]=1)#[N:4]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazoleHCID 178509733HCID 178509733, Verbindung

Produkt 1

HCID 545338182-[3-(4-Cyanostyryl)-1,2,4-triazol-1-yl]-1-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl methyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Sodium hydride (55% oil dispersion) (0.4 g.) was added to a solution of 3-(4-cyanostyryl)-1,2,4-triazole (1.6 g.) in dimethylformamide (20 ml.). After the effervescence had ceased, a solution of 2-(2,4-difluorophenyl)-2,3-epoxy-1-(1,2,4-triazol-1-yl)propane (1.9 g.) in dimethylformamide (10 ml.) was added, and the mixture was heated at 75° C. for 5 hours, then stirred at room temperature for 16 hours. The reaction mixture was diluted with water (150 ml.) and extracted with ethyl acetate (100 ml). The organic layer was washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was crystallised from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) to give 2-[3-(4-cyanostyryl)-1,2,4-triazol-1-yl]-1-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl methyl)ethanol, m.p. 189°-91° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue was crystallised from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-da0360a4b79e4fc09b5dd932d74ec914
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925863

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