Reaktion #989076

Reaktionsgleichung

aluminium chloride

4-chlorobenzonitrile

4-methylthioaniline

→

title compound

Ausbeute 43.4%

4-Chloro-N-[4-(methylthio)phenyl]benzenecarboximidamide

Ausbeute 43.4%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to 50° C
2. 2
   SonstigeThe resultant mixture was triturated with ethyl acetate
3. 3
   WaschenThe ethyl acetate layer was washed with water
4. 4
   Trocknendried over anhydrous sodium sulphate
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give the crude product, which
7. 7
   Sonstigewas purified by column chromatography

Vorschrift

Finely powdered anhydrous aluminium chloride (0.83 g, 6 mmol) was added to a stirred mixture of 4-chlorobenzonitrile (0.6875 g, 5 mmol) and 4-methylthioaniline (0.695 g, 5 mmol) over a period of 30 min. The reaction mixture was heated at 180-190° C. for 3 hours with stirring and allowed to cool to 50° C. The resultant mixture was triturated with ethyl acetate and basified with sodium hydroxide (20%) solution. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulphate and concentrated to give the crude product, which was purified by column chromatography to yield the title compound (0.6 g, 43.4%, purity 98.8% by HPLC), mp 148-150° C. 1H-NMR (CDCl3):δ 2.48 (s, 3H), 6.90-6.97(m, 2H), 7.11-7.41(m, 4H), 7.74 (bs, 2H). MS m/z:277.0 (M+)

Quelle