N-(3-Methylphenyl)urea → o-Tolyl Urea Styrene

Reaction equation

[C:1]1(C)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([NH2:10])=[O:9])[CH:2]=1.N[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1.[C:21]1(C)C=CC=C(N=C=O)C=1>C(Cl)(Cl)Cl>[CH2:18]=[CH:17][C:16]1[CH:19]=[CH:20][CH:13]=[CH:14][CH:15]=1.[C:2]1([CH3:21])[CH:1]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:7][C:8]([NH2:10])=[O:9]

Participants

Procedure

m-Tolyl Urea Styrerie: 1.00 g (8.40 mmol) of p-aminostyrene (99% Tokyo Kasei) was added to a 250 ml round bottom flask containing 10 ml of chloroform. After ten minutes of mixing, 1.12 g (8.41 mmol) of m-tolyl isocyanate (99% Aldrich) was added dropwise. Within seconds, a white, pinkish precipitate formed. Chloroform (20 ml) was added to aid stirring. The precipitate was filtered to remove the reaction liquid, then washed with 20 ml of chloroform resulting in a white powder (166 g, 78% crude yield, mp=203° C.).