Methanol → 3-(4-Chlorobenzylsulfanyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

3.17 g (20 mmol) of 4-chlorobenzylmercaptan are dissolved in 20 ml of methanol containing 3.60 g (20 mmol) of sodium methylate (30%), warmed to 50° C. and then evaporated. A solution of 4.68 g (15 mmol) of 3-chloro-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one in 20 ml of dimethylformamide is added. At the end of the exothermic reaction the solution is stirred at 100° C. for 1 hour and the solvent is evaporated. The residue is shaken with toluene/water, the organic phase is washed with water, dried and the reaction product is purified by flash column (150 g of silicagel) chromatography; elution with 1000 ml of toluene containing 10 and 20% of acetone. The fractions with TLC Rf-values 0.45 and 0.38 (toluene/acetone 7:3) are collected and evaporated.

Provenance & Evidence