Triethylamine → N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-4-chlorophenoxyacetamide

Participants

Reaction Steps

9.3 g (0.05 mol) of 4-chlorophenoxyacetic acid, 6.9 g (0.05 mol) of 1-(2-aminoethyl)-2,5-dimethylpyrrole and 35 ml of triethylamine are dissolved in 50 ml of dimethylformamide. At -5° to 0° C., 20 ml of methylethylphosphinic anhydride are added dropwise, and the mixture is then stirred at room temperature for 3 h. The reaction mixture is poured into ice-cold aqueous sodium bicarbonate solution, and the mixture is extracted with methylene chloride and the extract is concentrated. The residue is chromatographed over a 20 cm silica gel column using a 1:1 methylene chloride/ethyl acetate mixture as the mobile phase, and the product is crystallized using ligroin. Yield: 10.5 g (69% of theory), Melting point: 75°-77° C. Elemental analysis: C16H19CLN2O2 (306.80) calculated: C 62.6 H 6.2 CL 11.6 N 9.1 0 10.4 found: C 62.7 H 6.4 CL 11.7 N 9.2 0 10.4

Provenance & Evidence