Sodium Hydroxide → HCID 9819591, compound

Participants

Reaction Steps

While stirring under nitrogen, at minus 30°, a solution of 23 g (0.1 mol) of 4-chloro-5-cyano-2-methoxybenzoic acid chloride in 70 ml of methylene chloride is added dropwise to a solution of 11.6 g (0.1 mol) of 2-diethylaminoethylamine in 100 ml of methylene chloride. The resulting white suspension is then stirred at room temperature for 15 hours, 105 ml (0.105 mol) of 1M sodium hydroxide solution are then added dropwise thereto and the whole is stirred until 2 distinct layers have formed and then separated in a separating funnel, and the aqueous phase is again extracted by shaking with 50 ml of methylene chloride. The combined organic phases are dried over magnesium sulphate and filtered, 150 ml of cyclohexane are added and methylene chloride is distilled off until the distillation temperature is 70°. After cooling, the base that has crystallised out is filtered off with suction and then washed with cyclohexane. After drying, 4-chloro-5-cyano-N-(2-diethylaminoethyl)- 2-methoxybenzamide having a melting point of 104°-105° is obtained.

Provenance & Evidence