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

反応式

[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[N:2].[C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1)#[N:11].O>C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)=[O:20])[CH:7]=[CH:8][CH:9]=1)#[N:2]

参加物

実験手順

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).