Dimethylformamide → 1-[2-(Dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one

Participants

Reaction Steps

A mixture of N-[2-(dimethylamino)ethyl]benzene-1,2-diamine (3.11 g, 17.3 mmol) and 1,1-carbonyldiimidazole (CDI) (3.2 g, 19 mmol) are heated in DMF to 110°-120° C. until reaction is complete by TLC, cooled and extracted with EtOAc. The combined extracts are washed with water, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, 94:5:1 CH2Cl2, methanol, concentrated NH4OH as eluent) to give the title compound as a dark purple solid, 3.03 g (85% yield), identified by HPLC and mass spectral analyses.

Provenance & Evidence