Diisopropylcarbodiimide → ethyl (2-o-tolylamino-3H-benzimidazol-5-yl)acetate

Participants

Reaction Steps

A mixture of ethyl 3,4-diaminophenylacetate (5.8 g, prepared according to the procedure of Mederski et al, Bioorg Med Chem Left, 1998, 8, pages 17-22) and o-tolylisothiocyanate (4.9 g) in ethanol (100 mL) was kept at room temperature overnight then treated with diisopropylcarbodiimide (7.6 g). The mixture was stirred at reflux for 5 hours then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of 10% methanol and ether (1:9, v/v) to give the title compound (5.2 g) as a yellow gum.

Provenance & Evidence