2-Methylphenyl isothiocyanate → Ethyl 3-(2-o-tolylamino-benzoxazol-6-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-(4-amino-3-hydroxyphenyl)-propionate (1.94 g) in ethanol (50 ml) was treated with o-tolyl isothiocyanate (1.66 g) and then heated at 40° C. for 2 hours. The mixture was evaporated then treated with ethanol (50 ml), then with diisopropylcarbodiimide (3 mL) and then stirred at 40° C. for 1 hour. The mixture was evaporated and the residue was treated with diethyl ether (50 ml) then filtered. The filtrate was evaporated to dryness and the residue subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:3, v/v) to give the title compound (1.6 g) as a colourless oil.

Provenance & Evidence