Reaktion #2075727

Reaktionsgleichung

lithium bis(trimethylsilyl)amide

4-chloro-2-fluoro-3-methoxybenzonitrile

2-propanol

HCl

→

title compound

Ausbeute 156.9%

4-Chloro-2-fluoro-3-methoxybenzamidine hydrochloride

Ausbeute 156.9%

Lösungsmittel

ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITUpon standing at 5° C. for 18 h
2. 2
   Sonstigeprecipitated
3. 3
   FiltrationThe precipitated product was collected by filtration
4. 4
   Waschenwashed with ether
5. 5
   Sonstigedried under vacuum

Vorschrift

4-chloro-2-fluoro-3-methoxybenzonitrile (3.0 g, 16 mmol) was dissolved in 7 mL dry THF and added dropwise to a 1M solution of lithium bis(trimethylsilyl)amide (18 mL, 18 mmol). After stirring at 25° C. for 5 h, the mixture was treated with 25 mL of 2-propanol saturated with gaseous HCl. Upon standing at 5° C. for 18 h, the mixture was diluted with 30 mL ether whereupon the product precipitated. The precipitated product was collected by filtration, washed with ether and dried under vacuum to give the title compound (3.0 g, 78.6% yield): 1H NMR (DMSO-d6) δ 9.70 (br d, 3H), 7.58 (m, 1H), 7.46 (m, 1H), 7.39 (br d, 1H), 3.96 (s, 3H).

Quelle