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)+
REFERENCE
http://www.google.com/patents/WO2013124413A1?cl=en
TAKE A TOUR
St Maarten, Carribean.
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St. Maarten’s Extreme Airport: A Caribbean Paradise for Thrill Seekers, Aviation Enthusiasts
At Philipsburg, St. Maarten, Carribean.
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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)+
REFERENCE
http://www.google.com/patents/WO2013124413A1?cl=en
TAKE A TOUR
St Maarten, Carribean.
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Saint Martin Island has an extreme airport right next to the beach.
Posted by Konbini on Wednesday, March 4, 2015
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St. Maarten’s Extreme Airport: A Caribbean Paradise for Thrill Seekers, Aviation Enthusiasts
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At Philipsburg, St. Maarten, Carribean.
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