Water → 1-(3-Cyanophenyl)-3-(4-cyanophenyl)urea

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m-Cyanoaniline (0.5 g, 3.38 mmol) and p-cyanophenylisocyanate (0.49 g, 3.38 mmol) were dissolved in dimethylformaide (8 ml) and triethylamine (1 ml). The reaction was stirred at ambient temperature under a nitrogen atmosphere for 24 h. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with water (3×), brine, dried (MgSO4) and concentrated to give a amorphous solid. This was triturated to a crystalline white solid with ethyl ether. This solid was filtered and washed with ether to give N-(3-cyanophenyl)-N′-(4-cyanophenyl)urea as a white powder (0.92 g, mp 183-5° C.); LRMS (M+H)+ m/z 280, (M+NH4)+ m/z 297; 1H NMR (DMSO-d6): 9.32(s, 1H), 9.21(s, 1H), 7.97(s, 1H), 7.75-7.6(m, 5H), 7.55-7.4(m, 2H).

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