Benzene → 4-(2-chlorophenyl)-6,8-dimethyl-3-(3-methyl-4H-1,4-benzothiazin-2-carbonyl) aminoquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (1.0 g), triethylamine (2 drops) and benzene (5 ml) was heated to 70° C., and diketene (0.25 ml) was dropwise added thereto. The mixture was further heated at 70° C. for 30 minutes, and then, dimethylsulfoxide (15 ml) and 2-aminothiophenol (0.4 g) were added thereto. The resultant mixture was heated at 130° C. for an hour, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with a solution of salt and dried (MgSO4). The solvent was removed and the residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1,V/V), and then crystallized from ethyl acetate-ethyl ether to give 4-(2-chlorophenyl)-6,8-dimethyl-3-(3-methyl-4H-1,4-benzothiazin-2-ylcarbonyl) aminoquinoline (0.39 g, 26%) as yellowish prisms.

Provenance & Evidence