Réaction #2075727

Équation de réaction

lithium bis(trimethylsilyl)amide

4-chloro-2-fluoro-3-methoxybenzonitrile

2-propanol

HCl

→

title compound

Rendement 156.9%

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

Rendement 156.9%

Solvants

ether

THF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source