Hydrochloric Acid → 2-Chlorobenzimidamide

Participants

Reaction Conditions

Reaction Steps

According to literature reference (Huang, Y.; Luedtke, R. R.; Freeman, R. A.; Wu, L.; Mach, R. H. Bioorg. Med. Chem. 2001, 9, 3113–3122), to a solution of hexamethyldisilazane (36.7 mL, 175 mmol) in of diethyl ether (300 mL) at 0° C. is added n-butyl lithium (114 mL of 1.6 M solution in hexanes, 182 mmol) and the reaction mixture is stirred at 0° C. for 30 minutes after which time 2-chlorobenzonitrile (10.0 grams, 72.7 mmol) is added and the reaction mixture is warmed to 25° C. and stirred for 5 hours. Once complete, the reaction is poured into 2 N HCl and the aqueous phase was washed twice with diethyl ether. This aqueous phase is then made basic (pH=12) by addition of 6N sodium hydroxide. Subsequently, the aqueous phase is extracted with CH2Cl2 and the combined organic extracts are dried over sodium sulfate and concentrated to provide a crude solid. The crude product is then recrystallized from ethyl acetate to afford 5.4 g of 2-chlorobenzenecarboximidamide.

Provenance & Evidence