Tetrahydrofuran → 2-Fluoro-N-thiazol-2-yl-4-thioureido-benzenesulfonamide

Participants

Reaction Steps

Carbonothioic dichloride (25 uL, 0.00032 mol) was added to a mixture of the 4-amino-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (105 mg, 0.000271 mol) and N,N-diisopropylethylamine (0.14 mL, 0.00081 mol) in tetrahydrofuran (1.5 mL, 0.018 mol) at 0° C. and stirred for 40 min. Sat'd NH4OH solution was added to the reaction mixture and stirred for a few min. The reaction mixture was rotovaped to remove THF. The aq phase was acidified with 1.0 N HCl (pH 6), extracted with EtOAc (3×), dried, and was concentrated to give the crude product, which was purified via automated flash chromatography (silica gel, 25% EtOAc in hexanes to 100% EtOAc). 32 mg (36%) of the product was obtained as a yellow solid.

Provenance & Evidence