Thiazolidinedione → HCID 16392506, compound

Temperature

5 °C

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-thiazolidine-2,4-dione (10 g, 85.38 mmol, 1.00 equiv) in tetrahydrofuran (300 mL), 2-bromoethan-1-ol (10.6 g, 84.82 mmol, 1.00 equiv), triphenylphosphane (27 g, 102.94 mmol, 1.20 equiv). This was followed by the addition of a solution of DIAD (21 g, 103.96 mmol, 1.20 equiv) in tetrahydrofuran (30 mL) dropwise with stirring at 0-10° C. in 30 min. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/50) to give 9 g (47%) of 3-(2-bromoethyl)-1,3-thiazolidine-2,4-dione as a colorless oil.

1. customInto a 500-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred overnight at room temperature
4. concentrationThe resulting mixture was concentrated under vacuum
5. washeluted with ethyl acetate/petroleum ether (1/50)

ORD record

ord-8f97f7cf010243f989031386dcde54a4

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376438B2