[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24].C(N(CC)CC)C>C(Cl)Cl>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1)=[O:24]Route 2: 2-(4-aminophenyl)-6-methyl benzothiazole (2.0 g, 8.3 mmole) and 2-Furoyl chloride (1.086 g, 8.32 mmole) were suspended in methylene chloride (30 ml, anhydrous). triethylamine (1.24 g, 12.25 mmole) was added to the reaction mixture with stirring at room temperature for 2 days. (pH 7.0-7.2). Methylene chloride (50 ml) was added to the reaction mixture, and the reaction mixture extracted with 1 N HCl (50 ml) to separate a solid. The solid was filtered and washed with water to yield 1.3 g (46%) of the desired compound. The product was crystallized from MeOH to obtain 0.99 g, mp 238-240° C. 1H and 13C NMR were consistent with the expected product. TLC showed one spot (5% MeOH-CH2Cl2 as developing solvent on silica gel plate).
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