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

Participants

Reaction Steps

N-Ethyl-N-(1,3-dioxolan-2-ylmethyl)amine (1.31 grams; 0.01 mole), toluene (40 ml) and triethylamine (3 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer, thermometer and addition funnel. A solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (4.2 grams; 0.01 mole) in toluene (30 ml) was added dropwise, with stirring at room temperature. A slight exotherm was observed. After the addition was completed stirring was continued for a period of about 1.5 hours. After this time the reaction mixture was transferred into a separatory funnel and was washed twice with water (60 ml), with dilute aqueous sodium bicarbonate (60 ml; 5% conc.) and again with water (60 ml). The washed organic phase was dried by passing it through phase separation paper and was thereafter stripped of solvent leaving a viscous oil as the residue. This residue was subjected to chromatography using a clay column (150 ml) and mixtures of ethyl acetate and hexane with increasing concentrations of ethyl acetate as the eluant. Nine fractions were collected. Fractions six and seven were combined and stripped of solvents to yield the desired product N-ethyl-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as an amber gum.

Provenance & Evidence