Toluene → HCID 54417945, compound

Participants

Reaction Steps

A mixture of 1.46 g (0.011 mol) of rhodanine, 2.34 g (0.01 mol) of 1-(3,4-dimethoxyphenyl)-1-hexen-3-one, 0.77 g (0.01 mol) of ammonium acetate and 20 ml of toluene was heated under reflux for 8 hours. After cooling, 100 of water were added to the reaction mixture, and the layers were then extracted with chloroform (80 ml×3). A chloroform layer was washed twice with water and once with a saturated aqueous solution of sodium chloride. The chloroform layer was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give a reddish brown oily substance. The oily substance was purified by silica gel column chromatography (eluent, chloroform:methanol=150:1) to give 0.03 g of the isomer A of the desired 5-(α-propyl-3,4-dimethoxycinnamylidene)-4-oxo-2-thioxothiazolidine from the first eluate and 0.2 g of the isomer B from the subsequent eluate.

Provenance & Evidence