Cl[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[CH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[CH:5][CH:4]=1.NC(N)=[S:23].[OH-].[Na+].S(=O)(=O)(O)O>CCOCC.ClCCl.C(O)C>[SH:23][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[CH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[CH:5][CH:4]=1
A solution of 4'-chloromethyl-2,5-dimethoxystilbene (856 mg, 2.96 mmol), thiourea (0.29 g, 3.8 mmol), and ethanol (16 ml) was heated to reflux for 3.5 h. Aqueous sodium hydroxide (2.5 M, 2.8 ml) was added and the mixture refluxed for further 2 h. The reaction mixture was allowed to cool and dichloromethane (50 ml), ether (200 ml) and sulfuric acid (10%, 10 ml) were added. The organic layer was separated, washed with water (2×200 ml), brine (100 ml), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1) to give (32b) (328 mg, 39%); νmax /cm-1 2950s, 1490m, 1470s, 1430m, 1390s, 1215s, 1180s, 1050s.
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