Dichloromethane → 1-(4-Ethynylphenyl)-3-(3-methylphenyl)urea

Participants

Reaction Steps

A solution of 4-ethynylaniline (1.308 g, 11.18 mmol, 1 eq) and m-tolyl isocyanate (1.684 mL, 1.2 eq) in anhydrous THF (20 mL) was stirred under nitrogen atmosphere at room temperature for three hours. The yellow solution was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The clear solution was decanted, concentrated under reduced pressure to a lesser amount, and an off-white solid was obtained upon filtration. This solid was subject to a gradient column chromatography (EtOAc-Hex 1:100 to 1:4) followed by another column chromatography (from DCM to MeOH-DCM 1:10). 1-(4-ethynylphenyl)-3-(3-methylphenyl)urea was obtained as an off-white powder in amount of 2.134 g.

Provenance & Evidence