Cyanogen Bromide → 2,4,6-Trimethylphenyl(imino)imidazolidine
Reaction equation
[N:1]#[C:2]Br.[CH3:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[NH:13][CH2:14][CH2:15][NH2:16]>C(O)C>[CH3:12][C:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]([CH3:4])[C:6]=1[N:13]1[CH2:14][CH2:15][N:16]=[C:2]1[NH2:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of cyanogen bromide (1.8 g, 18.5 mmol) in anhydrous ethanol (3 mL) was added at 0° C. to a solution of N1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diamine (3.0 g, 16.9 mmol) in anhydrous ethanol (9 mL) under nitrogen. The reaction mixture was warmed up to room temperature for 10 min, then was heated at 155° C. for 40 min with a flow of nitrogen to remove ethanol. Upon cooling to r.t., the resulting solids were transferred to a separatory funnel via dichloromethane (70 mL), and washed sequentially with 1 N sodium hydroxide (2×35 mL), water and brine. The organic layer was dried over anhydrous sodium sulfate and solvents were removed in vacuo to afford the title compound as a pale white solid (3.08 g, 90% yield). The solids were used for the next step without further purification.