1,1'-Carbonyldiimidazole → HCID 59333298, compound

Participants

Reaction Steps

To a solution of 5-bromo-2-imidazol-1-yl-phenylamine (5.00 g; 21 mmol; 1 eq) in anhydrous dichlorobenzene (410 mL), is added carbonyldiimidazole (6.94 g; 42 mmol; 2 eq) under argon atmosphere. This reaction mixture is allowed to stir under reflux for 2 hours. The initial crystal clear solution quickly turns black after heating and become non homogeneous. This crude reaction mixture is allowed to cool to room temperature and the grey powder formed during the reaction is filtered off on a fritted glass. The filtrate is cooled down to 0° C. overnight to afford a second batch of grey powder. The combined 6.5 g of grey solid is transferred in a 1 L flask, diluted in fresh ethyl acetate (500 mL) and heated to gentle reflux for ten minutes. Hot filtration followed by concentration afforded the title compound as a grey powder (3.85 g; 14.6 mmol; 69%).

Provenance & Evidence