Hydrochloric Acid → N-(3,4-Dichlorobenzoyl)glycine

Participants

Reaction Conditions

Reaction Steps

To glycine (3.6 g, 47.7 mmol) in acetonitrile (100 mL) at ambient temperature was added 2N aqueous sodium hydroxide (60 mL, 120 mmol). The reaction mixture was cooled to about 0° C. and 3,4-dichlorobenzoyl chloride (10 g, 47.7 mmol) in acetonitrile (20 mL) was added slowly over about 5 minutes. The reaction mixture was stirred for about 30 minutes at 0° C. then the pH of the reaction mixture was adjusted to 3 by addition of 3N aqueous hydrochloric acid. The organic solvent was removed in vacuo and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with brine (30 mL), dried over MgSO4 and concentrated in vacuo to afford a light yellow solid. The crude material was triturated with toluene (100 mL) and washed with cold toluene (3×100 mL). The resulting white solid was recrystallized from ethyl acetate to afford 2-(3,4-dichlorobenzamido)acetic acid (4.9 g, 42%) as a white solid. RP-HPLC (table 1, Method b) Rt 1.45 min; m/z: (M+H)+ 246.

Provenance & Evidence