C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:7][S:8][C:9]=1[C:10]([O:12]C)=[O:11])=[O:4].[OH-].[Na+].Cl>O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:5]([C:3]([OH:4])=[O:2])=[C:9]([C:10]([OH:12])=[O:11])[S:8][N:7]=2)=[CH:19][CH:18]=1A solution of 4.4 g of 5 and 2.8 g of NaOH in 20 ml of water is kept at reflux for 2.5 h. The reaction mixture is cooled, diluted with water (150 ml) and acidified with conc. HCl (aq). A precipitate forms. The water layer is extracted with EtOAc (2×200 ml; the precipitate slowly dissolves). The combined organic layers are washed with brine and dried (Na2SO4). Concentration afforded 3.9 grams of 6 as a white solid.
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