[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([SH:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.C[O-].[Na+].[Cl:16][C:17]1[CH:18]=[C:19]([CH2:23][NH:24][C:25](=[O:28])[CH2:26]Cl)[CH:20]=[CH:21][CH:22]=1.C(O)(=O)C>CO.O>[OH:9][C:7]1[C:6]2[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[S:12][C:26]=1[C:25]([NH:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=1)=[O:28]
To a solution of methyl 5-chloro-2-mercaptobenzoate (1.02 g; 0.005M) in 20 ml of methanol is added solid sodium methoxide (0.81 g; 0.015M; 3 eqv.) followed by N-[(3-chlorophenyl)methyl]chloroacetamide (1.10 g; 0.005M) and the mixture is refluxed under a nitrogen atmosphere for 30 minutes. The mixture is cooled to room temperature and added to a solution of 1.25 ml of glacial acetic acid in 20 ml of water and cooled to 0° C. The white solid is collected, washed with 50% methanol-water and air dried to give 1.60 g (91% yield) of the title compound; m.p. 184°-186° C.
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