5-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride → 5-(4-{2-[1-(2',5'-Dimethoxybiphenyl-4-yl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dione

Participants

Reaction Steps

Following a procedure similar to that described in Example 40(f), 256 mg of 4'-(2,5-dimethoxyphenyl)acetophenone were reacted with 382 mg of 5-[4-(2-aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)]. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was extracted with ethyl acetate. The extract was washed with water and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 2:3 by volume mixture of ethyl acetate and hexane as the eluent, to give 482 mg of the title compound as an amorphous solid, melting at 47-52° C. (softening point).

Provenance & Evidence