[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[S:9]1[CH2:13][C:12](=[O:14])[NH:11][C:10]1=[O:15].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:13]2[S:9][C:10](=[O:15])[NH:11][C:12]2=[O:14])[S:5][CH:6]=1To a mixture of 4-bromothiophene-2-carboxaldehyde (1.91 g, 10.0 mmol) and 2,4-thiazolidinedione (1.40 g, 12.0 mmol) in ethanol (30 mL) was added piperidine (1.0 mL, 10.0 mmol). The reaction mixture was heated at reflux for 3 h, then cooled on an ice-bath, and the precipitated products were collected by filtration. The cake was washed with 40% ethanol and dried to afford 5-(4-bromothiophen-2-ylmethylene)-2,4-thiazolidinedione (2.53 g, 87%).
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