Ammonium Chloride → HCID 86725869, compound

Participants

Reaction Steps

To a stirred suspension of NH4Cl (3.58 g, 66.37 mmol) in dry toluene (100 mL) was added trimethyl aluminium (2M in toluene, 33.18 mL, 66.37 mmol) at 5° C., then the mixture was warmed to room temperature and stirred for 2 h. A solution of (2-bromo-5-methoxy-phenyl)-acetonitrile (136) (5 g, 22.12 mmol) in toluene (25 mL) was added to the above reaction mixture and the mixture was then stirred for 14 h at 80° C. After completion of the reaction, it was quenched with a suspension of silica gel in chloroform and the reaction mixture was stirred for half an hour at room temperature and filtered through a sintered funnel, the silica gel was washed with methanol and the combined filtrate was concentrated under reduced pressure to get 2-(2-bromo-5-methoxyphenyl)-acetamidine hydrochloride salt as a crude product (137) (4 g, 74.37%) a as white solid.

Provenance & Evidence