Réaction #77983

Équation de réaction

ethyl 3,4-diaminophenylacetate

o-tolylisothiocyanate

diisopropylcarbodiimide

→

title compound

Ethyl (2-o-tolylamino-3H-benzimidazol-5-yl)acetate

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Autreprepared
2. 2
   workup.WAITLeft
3. 3
   Températureat reflux for 5 hours
4. 4
   Autrethen evaporated
5. 5
   workup.ADDITIONThe residue was subjected to flash chromatography on silica eluting with a mixture of 10% methanol and ether (1:9, v/v)

Mode opératoire

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.

Source