Hydrochloric Acid → HCID 19754881, compound

Participants

Reaction Steps

A slurry of cuprous oxide (1.00 g, 6.78 mmol) in a solution of 3,4,5-trimethoxyphenol (1.62 g, 8.53 mmol) and 4-bromo-3-methoxybenzoic acid N-isopropyl-N-cyclohexyl amide (2.42 g, 6.8I mmol) in 2,4,6-collidine (30 ml) was refluxed with stirring under a nitrogen atmosphere for 36 hr. Additional 3,4,5-trimethoxyphenol (0.32 g), and cuprous oxide (0.16 g) were added and reflux continued for 72 hrs. The reaction mixture was cooled, poured onto 6N HCl and extracted three times with ethyl acetate. The combined organic layers were washed twice with 5% NaOH solution, twice with saturated NaCl solution and dried (Na2SO4) The drying agent was filtered and the filtrate concentrated in vacuo to give 1.29 g of crude product. This material was chromatographed twice on silica gel using mixtures of ethyl acetate and hexane as the eluents to give the title compound as a crystalline solid that could be recrystallized from ethyl acetate hexane, m. pt. 126-128° C.

Provenance & Evidence