Water → 5-(2-chloro-6-fluorophenyl)-3-(4-chloro-alpha,alpha-dimethylbenzyl)-1-methyl-1H-1,2,4-triazole

HRID 443045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443045
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:7])[C:3](Cl)=[N:4][NH2:5].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:17]=1[C:18]#[N:19].[Cl-].[Al+3].[Cl-].[Cl-].O.Cl[C:31]1C=CC=CC=1Cl>>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:17]=1[C:18]1[N:5]([CH3:31])[N:4]=[C:3]([C:2]([CH3:7])([CH3:1])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:19]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 72391,2-DichlorobenzeneHCID 695872-Chloro-6-fluorobenzonitrileHCID 6451240Aluminum(III) ChlorideHCID 86754043alpha, alpha-Dimethyl-4-chlorophenylacetohydrazonoyl chloride

Produkt 1

HCID 542307375-(2-chloro-6-fluorophenyl)-3-(4-chloro-alpha,alpha-dimethylbenzyl)-1-methyl-1H-1,2,4-triazole

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 0.7 g of N-methyl-N-(p-toluenesulfonyl)-(α, α-dimethyl-4-chlorophenylacetohydrazonoyl chloride in 7 ml of o-dichlorobenzene at room temperature, were added 0.33 g of 2-chloro-6-fluorobenzonitrile and 0.28 g of anhydrous aluminium chloride, and the reaction mixture was heated at 120° C. for 30 minutes. After cooling, the reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 0.6 g of 5-(2-chloro-6-fluorophenyl)-3-(4-chloro-α,α-dimethylbenzyl)-1-methyl-1H-1,2,4-triazole. m.p.97°-100° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d78e0ccdc1964e0599130b92559e95f0
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892048

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