[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.BrCC([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)=O.O.OS(O)(=O)=O.[CH2:30](O)[CH3:31]>[Fe]>[N:1]1[C:30]([NH:21][C:18]2[CH:17]=[CH:16][CH:15]=[CH:20][CH:19]=2)=[CH:31][N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[S:3][C:2]=12A mixture of 2-aminobenzothiazole (4.00 g, 26.6 mmol) and 2-bromo-4′-nitroacetophenone (7.32 g, 30.0 mmol) was refluxed in ethanol for 90 min and then the mixture was cooled to 0° C. The solid (about 2 g) was collected by filtration, washed with the minimum quantity of cold ethanol and then dissolved again in 150 ml of ethanol and added of iron powder (7.47 g, 133.75 mmol), water (30 ml) and H2SO4 12N (750 μl). The mixture was stirred at 90° C. for 1 h, then filtered on celite and washed with hot ethanol. The solvent was removed under reduced pressure and the crude material was treated with aqueous NaHCO3 (10%, 400 ml) and extracted with CH2Cl2 (3×150 ml). The organic phase was dried with anhydrous Na2SO4 and the solvent removed under reduced pressure to afford 4-[(imidazo[2,1-b]benzothiazol-2-yl)aniline.
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