[OH-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[S:7][C:8]=1[C:9]([O:11]CC)=[O:10].Cl.C(O)(=O)C>O.C(O)C>[CH3:3][C:4]1[N:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[S:7][C:8]=1[C:9]([OH:11])=[O:10]
A solution of sodium hydroxide (22 g. 0.55 mole) in water (300 ml.) was mixed with a solution of ethyl 4-methyl-2-(3-pyridyl)-5-thiazolecarboxylate (124 g., 0.50 mole) in 95% ethanol (150 ml.). The mixture was heated and stirred for about ten minutes on a steam bath, and then allowed to stand for one hour without further heating. When the ice-cooled reaction mixture was neutralized with dilute hydrochloric acid and acidified with acetic acid, a thick precipitate of finely divided white solid was obtained. The solid was collected by filtration, washed thoroughly with water, and dried in an oven at 110° C. The product (106 g., 96% yield) melted with decomposition at 249°-250° C.
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