Potassium Hydroxide → HCID 15670615, compound

Participants

Reaction Steps

Potassium hydroxide (2.47 g, 44.0 mmol) was added to a suspension of 5-[(6-ethoxycarbonyloxy-2-naphthalenyl)thio]-2,4-thiazolidinedione (8.0 g, 22 mmol) in methanol (50 mL) at 25° C. After 30 minutes, the resulting solution was acidified to pH=1 with and then extracted with ethyl acetate (3×). The combined extracts were dried (magnesium sulfate) and concentrated to give 5-[(6-Hydroxyl-2-naphthalenyl)thio]-2,4-thiazolidinedione as a powder (6.4 g, 99% yield): mp 182°-183° C. (chloroform/ethyl acetate); 1H NMR (DMSO-d6, 400 MHz) δ 6.07 (s, 1 H CH). 7.1-8.0 (m, 6 H, ArH). Analogue 35 was prepared similarly, with the use of 3 molar equivalents of potassium hydroxide.

Provenance & Evidence