2-benzyl-4-(2-hydroxy-ethyl)-[l,2,4]thiadiazolidine-3,5- dione

2-benzyl-4-(2-hydroxy-ethyl)-[l,2,4]thiadiazolidine-3,5- dione (Compund 4).

To a suspension of benzoic acid 2-(2-benzyl-3,5-dioxo-[l,2,4]thiadiazolidin-4-yl) ethyl ester (74.0 g, 207.6 mmol) in methanol (740mL) 12N HC1 (740 mL) was added at room temperature. The mixture was heated at 50°C for 18 h, then additional 12N HC1 (250 mL) was added and the mixture was stirred for 84 hours at 40 °C until hydrolysis was completed. The mixture was concentrated at reduced pressure to remove the methanol, and the resulting mixture was extracted with methylene chloride (3 x 500 mL). The combined organic layers were dried (Na₂S0₄), filtered and evaporated to yield an oil that was treated with hot ethyl acetate (200 mL) and precipitated by the addition of n- heptane (200 mL) to yield the pure desired product as a white solid (42.5 g, 81%)
1H NMR (400 MHz, DMSO-d₆, δ ppm): 7.41-7.31 (m, 5H), 4.91 (t, J = 5.85 Hz, 1H), 4.80 (s, 2H), 3.66 (m, 2H), 3.58 (m, 2H).
¹³C NMR (100 MHz, DMSO-d₆, δ ppm): 165.77, 152.87, 135.47, 128.67, 128.09, 127.96, 57.08, 47.33, 44.58.
MS (ES⁺): m/z = 253 (M+H)⁺





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