Cl.[CH3:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]1=[N:12][NH2:13].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.[OH-].[Na+]>C(O)(=O)C>[CH3:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5]/[C:4]/1=[N:12]/[N:13]=[CH:20][C:16]1[CH:17]=[CH:18][CH:19]=[N:14][CH:15]=11.50 g (6.42 mmol) of 2,3-dihydro-3-methyl-2-benzothiazolone hydrazone hydrochloride and 0.69 g (6.42 mmol) of 3-pyridinecarboxaldehyde in 10% acetic acid were stirred at room temperature for 30 minutes. The mixture was then made slightly alkaline with 2N sodium hydroxide solution and the precipitate was suction-filtered off, washed with water and dried under vacuum.
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