Water → HCID 69329102, compound

Participants

Reaction Steps

A 500-mL round bottomed flask under N2 equipped with overhead stirrer, a condenser, thermocouple and 100 mL dropping funnel was charged with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (21.17 g, 0.11 ml) and THF (140 mL). A solution of cyanoacetic acid (10.03 g, 0.118 mol) and 3-chloro-4-fluoroaniline (15.44 g, 0.106 mol) in THF (60 mL) was added to the dropping funnel and added to the reaction flask at 25-45° C. At the end of the addition the reaction became a clear solution. The solution was stirred at ambient temperature for 1.5 hours then poured slowly into water (500 mL) forming a white suspension. The suspension was stirred at room temperature overnight then filtered and the filter cake washed with water and dried under vacuum (50 mm Hg) at 45° C. to provide (3-chloro-4-fluorophenyl)-2-cyanoacetamide as a white solid (21.27 g, 94% yield, 97.5% by HPLC). 1H NMR (300 MHz, DMSO-d6): 10.4 (s, 1H), 7.80 (d, J=8 Hz, 1H), 7.5-7.3 (m, 2H), 3.92 (s, 2H).

Provenance & Evidence