[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:21]#[N:22])[C:18]=1[O:19]C)[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8]1)=[O:6].[Cl-].[Li+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:21]#[N:22])[C:18]=1[OH:19])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8]1)=[O:6]3-(3-chloro-5-cyano-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole (213 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (111 mg) was added to the solution, and then the mixture was stiffed at 100° C. for 2 hours. To the reaction solution, 1N hydrochloric acid was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1), and then crystallized from n-hexane-chloroform to obtain the title compound (68 mg) as a pale yellow crystal.
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