Hydrochloric Acid → 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 1848292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848292
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])(=[O:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH:21]=[C:22]([Cl:24])[CH:23]=1.C(N(CCCC)CCCC)CCC.Cl>O.C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]([C:25]([OH:30])([C:26]([F:27])([F:28])[F:29])[CH2:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)=[C:8]([CH:11]=2)[C:9]#[N:10])=[O:3])[CH:21]=[C:22]([Cl:24])[CH:23]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7622TributylamineHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 537719805-acetyl-2-(1H-1,2,4-triazol-1-yl)benzonitrile

Produkt 1

HCID 686135575-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1.00 g (4.71 mmol) of 5-acetyl-2-(1H-1,2,4-triazol-1-yl)benzonitrile, 1.15 g (4.71 mmol) of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 2.30 g of toluene and 0.26 g (1.41 mmol) of tributylamine were fed and the mixture was stirred for 24 hours at 60° C. The mixture was cooled to room temperature, and a separation operation was performed by adding 20 ml of toluene and an aqueous solution prepared with 0.15 g (1.41 mmol) of 35% hydrochloric acid and 10 ml of water. The toluene phase was washed with 10 ml of water. After removing the solvent by distilling under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1.20 g of 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile (yield 56.0%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washThe toluene phase was washed with 10 ml of water
  3. customAfter removing the solvent
  4. distillationby distilling under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a7b183468bc04763b64a53d93dc68d98
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952175B2

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