Propanal → HCID 18331459, compound

Participants

Reaction Steps

To a mixture of propionaldehyde (72 μl), chloroform (1 ml) and 1,4-dioxane (1 ml), bromine (52 μl) was added. The reaction mixture was stirred at room temperature for 30 min and then N-(3-(t-butoxycarbonylaminomethyl)phenyl)thiourea (262 mg), acetone (2 ml) and triethylamine (0.14 ml) were added. The reaction mixture was heated under reflux for 3.5 h and concentrated under reduced pressure. To the resulting residue, water was added and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (eluent, methylene chloride:methanol=99:1) to give 79.2 mg of the titled compound (yield, 27%).

Provenance & Evidence