[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9]C.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(=S)=S>[OH:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:6][C:7]=1[O:11][CH3:12]A solution of 2-(3,4,5-trimethoxyphenyl)benzothiazole (4.0 g), aluminium trichloride (4.0 g) and carbon disulphide (75 cm3) was stirred at room temperature overnight. The reaction mixture was poured onto 20% hydrochloric acid (500 cm3) and extracted with ethyl acetate (3×50 cm3). The combined organic extracts were washed with water (2×250 cm3), dried (MgSO4), filtered and the filtrate evaporated down under reduced pressure. The solid residue was recrystallised from ethyl acetate to give 3.0 g (75.0%) of the desired product.
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