Hydrochloric Acid → 3-Cyano-N-1,2,4-thiadiazol-5-yl-4-{[2-(trifluoromethyl)phenyl]thio}benzenesulfonamide

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Reaction Steps

2-Trifluoromethylthiophenol (0.0615 g, 0.345 mmol) and potassium carbonate (0.100 g, 0.724 mmol) were stirred in N,N-dimethylacetamide (3 mL). After 5 minutes, 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.150 g, 0.345 mmol) was added to the reaction mixture and the mixture stirred at ambient temperature overnight. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with a 1M aqueous solution of sodium hydroxide, followed by brine, then dried over MgSO4, filtered and concentrated in vacuo to give a residue. The residue was then dissolved in 1,4-dioxane (1 mL) and a 4M solution of hydrogen chloride in 1,4-dioxane added. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo to give a residue. The residue was solubilised in dimethylsulfoxide (1 mL) and purified by the B-HPLC method to afford the title compound.

Provenance & Evidence