[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].[CH:13](N(CC)C(C)C)(C)C.ClCOC.[OH-].[Na+].Cl>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1
12.05 g of 4-methoxysalicylic acid was dispersed in 200 ml of methylene chloride in argon atmosphere. To the dispersion were added 27.70 g of N,N-diisopropylethylamine and 19.20 g of chloromethylmethyl ether, and the mixture was agitated for 42 hours. The reaction mixture was poured into water, and extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and 300 ml of methanol was added to the residue. To the mixture was added a solution which has been prepared by dissolving 8.50 g of sodium hydroxide in 20 ml of water. The mixture was agitated for 20 hours, neutralized with 6N aqueous hydrochloric acid, and the solvent was distilled off in evacuated atomosphere. The mixture was adjusted to pH 1 with 1N aqueous hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off in evacuated atomosphere to produce 15 g of 4-methoxy-2-methoxy benzoic acid. To the product were added 8.50 g of 2-mercaptothiazoline, 15.34 g of N,'N-dicyclohexylcarbodiimide, 0.86 g of 4-dimethylaminopyridine, and 400 ml of 1,2-dichloroethane, and the mixture was agitated for 18 hours. The reaction mixture was filtered and the precipitate was washed with benzene. The filtrate and the wash liquid were combined, washed with 2N aqueous solution of sodium hydroxide, water, and saturated aqueous solution of sodium chloride in this order, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to a column chromatography using silica gel. There was obtained 12.36 g of N-(4-methoxy-2-methoxymethoxybenzoyl)thiazolidine-2-thion from fractions eluted with methylene chloride.
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