4-Aminophenol → 1-(Cyclopropylmethyl)-3-(4-hydroxyphenyl)urea

Participants

Reaction Steps

4-Aminophenol (18.33 mmol, 2 g) and 4-nitrophenyl carbonochloridate (18.33 mmol, 3.69 g) in dichloromethane (10 mL) were stirred at room temperature for 30 minutes. Cyclopropylmethanamine (36.7 mmol, 3.72 mL, 2.61 g) was added followed triethylamine (55.0 mmol, 7.66 mL, 5.56 g). The reaction was allowed to stir at room temperature overnight. The reaction mixture was diluted with dichloromethane/saturated sodium hydrogen carbonate solution and filtered through a hydrophobic frit. The organic layer was concentrated and the residue was purified by silica column chromatography (eluent: 2-8% methanol in dichloromethane) to give the title compound (1.4 g). MS (ESI) m/z 207.1 [M+H]+

Provenance & Evidence