Triethylamine → N-propyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

Participants

Reaction Steps

N-n-Propyl-N-(1,3-dioxolan-2-ylmethyl)amine (1.33 grams; 0.0092 mole), dry toluene (60 ml) and triethylamine (3.0 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer, thermometer and addition funnel. The reaction mixture was blanketed under nitrogen gas and a solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (3.9 grams; 0.0092 mole) in toluene (40 ml) was added dropwise with stirring. A slight exotherm was observed. After the addition was completed stirring was continued at room temperature for a period of about 1.5 hours. After this time the reaction mixture was transferred to a separatory funnel and was washed with water and dilute aqueous sodium bicarbonate. The washed solution was then dried and stripped of solvent leaving a viscous oil as the residue. This residue was then chromatographed through clay using ethyl acetate-hexane mixtures with increasing concentrations of ethyl acetate as the eluant. A total of nine fractions were collected. Fractions 5 and 6 were combined and stripped of solvents to yield the desired product N-propyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as an amber gum.

Provenance & Evidence