3-(4-Hydroxyphenyl)-2-thioxo-4-thiazolidinone → 5-[4-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-3-methoxyphenylmethylene]-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one

Participants

Reaction Steps

3-(4-Hydroxyphenyl)-2-thioxothiazolidin-4-one (0.23 g, 1.0 mmol) was added to a stirred suspension of 4-formyl-2-methoxyphenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (1b)(0.32 g, 0.9 mmol) in absolute ethanol (10 ml) containing ammonium acetate (0.08 g, 1.0 mmol) and the pale yellow heterogeneous reaction mixture boiled gently. After 5 h the mixture was cooled in ice and the yellow product was filtered off and washed well with methanol and acetone to give 5b (0.42 g, 74%), m.p. 234°-236° C., [α]D +2.5° (c 0.81, DMOS) Found: C, 53.62; H, 4.65; N, 4.73, C25H26N2O9S2 calc: C, 53.38; H, 4.63; N, 4.98).

Provenance & Evidence