Water → 2-(2-Propenylthio)-4-(4-trifluoromethylphenyl)benzonitrile

HRID 25277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25277
[SH:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:20][C:21](C)([O-])[CH3:22].[K+].O>CN(C)C=O>[CH2:22]([S:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH:21]=[CH2:20]

Komponenten

5

Edukt 3

HCID 962WaterHCID 121376372-Mercapto-4-(4-trifluoromethylphenyl)benzonitrileHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 121376382-(2-Propenylthio)-4-(4-trifluoromethylphenyl)benzonitrileAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.0 g (3.6 mmol) of 2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile, 0.45 g (4.0 mmol) of potassium tert-butoxide and 0.5 g (4.1 mmol) of 3-propenyl bromide were stirred in 20 ml of N,N-dimethylformamide at room temperature for 1 hour. The resulting reaction mixture was poured into 20 ml of water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.5 g of 2-(2-propenylthio)-4-(4-trifluoromethylphenyl)benzonitrile (yield 43.0%) as yellow crystals (m.p. 89-90° C.).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with 50 ml of ethyl acetate twice
  3. washThe ethyl acetate layer was washed with 50 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b4e50137f9a74103aa1c4fce791b62ea
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858639B2

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