4-Chlorobenzenesulfonyl chloride → 4-Chloro-N-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]benzenesulfonamide hydrochloride

Participants

Reaction Steps

To a mixture of 5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.4 g), N,N-diisopropylethylamine (0.27 g) and anhydrous N,N-dimethylformamide (15 ml) was added 4-chlorobenzenesulfonyl chloride (0.15 g) and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated and diluted with water and tetrahydrofuran and then extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. To a solution of the residue in tetrahydrofuran (10 ml) was added 4N hydrogen chloride in ethyl acetate (5 ml) and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added diethyl ether (10 ml) and this mixture was stirred at room temperature for 30 minutes and then was irradiated with ultrasound for 30 minutes. The precipitate was isolated by filtration and washed with acetone, ethyl acetate and n-hexane to afford the title compound (0.3 g, mp 155-160° C.).

Provenance & Evidence