1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58674703, compound

Participants

Reaction Conditions

Reaction Steps

(2E)-2-(3-methoxybenzylidene)butanoic acid (190 mg, 0.92 mmol), 4-chloro-3-(trifluoromethyl)aniline (189 mg, 0.97 mmol) and DMAP (135 mg, 1.11 mmol) were mixed together and stirred in DCM (15 mL). The reaction mixture was cooled to 0° C. and EDCI (118 mg, 1.29 mmol) was added. The reaction was allowed to warm slowly to rt overnight. The mixture was diluted with DCM and washed with 1N HCl, sat. NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (SiO2, 0-15% EtOAc in hexanes) to give the title compound (216 mg). 1H NMR (400 MHz, d6-DMSO): δ 10.44 (s, 1H), 8.29 (d, 1H), 8.05-8.02 (dd, 1H), 7.68 (d, 1H), 7.39-7.35 (m, 1H), 7.22 (s, 1H), 6.99 (d, 1H), 6.95-6.93 (m, 2H), 3.77 (s, 3H), 2.54 (q, 2H), and 1.08 (t, 3H).

Provenance & Evidence