Sodium hydride → 2-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile

HRID 1082074

Reaktionsgleichung

Reaktionsgleichung von HRID 1082074
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[SH:12].[H-].[Na+].F[C:16]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[S:12][C:16]1[C:23]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 880422-Amino-4-(trifluoromethyl)benzenethiolHCID 5189742-Fluoro-3-(trifluoromethyl)benzonitrile

Produkt 1

HCID 199694362-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrileAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2-Amino-4-trifluoromethylthiophenol (5.74 g, 25 mmol) was added to a mixture of sodium hydride (2.0 g of 60% oil dispersion, 50 mmol) in DMF (100 ml) at 0° under nitrogen. After stirring for 30 minutes at 0°, 2-fluoro-3-trifluoromethylbenzonitrile (4.73 g, 25 mmol) in DMF (20 ml) was added and the mixture kept at room temperature overnight. The reaction mixture was evaporated and azeotroped with toluene, then the residue was partitioned between chloroform and water and the layers separated. Drying (magnesium sulphate) and evaporation of the organic layer gave a residue which was purified by chromatography on silica gel, eluting with dichloromethane. Recrystallisation from cyclohexane afforded the product as colourless needles (6.44 g).

Aufarbeitung

  1. waitthe mixture kept at room temperature overnight
  2. customThe reaction mixture was evaporated
  3. customazeotroped with toluene
  4. customthe residue was partitioned between chloroform and water
  5. customthe layers separated
  6. customDrying
  7. custom(magnesium sulphate) and evaporation of the organic layer
  8. customgave a residue which
  9. customwas purified by chromatography on silica gel
  10. washeluting with dichloromethane
  11. customRecrystallisation from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-41f95da196dc4a58af01338051334978
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589474

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