Isopropyl Isothiocyanate → N-[5-Chloro-3-(isopropylthiocarbamoyl)sulfamoylthiophen-2-yl]acetamide

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Potassium tert-butoxide (135 mg, 1.2 mmol) was added to a solution of N-(5-chloro-3-sulfamoylthiophen-2-yl)-acetamide(255 mg, 1.0 mmol) in dry N,N-dimethylformamide (5 ml) with stirring on an ice bath. After 5 min, isopropyl isothiocyanate (0.128 ml, 1.2 mmol) was added dropwise and the solution was stirred for 30 min at 0° C. and then at room temperature for 3 h. A further amount of potassium tert-butoxide (135 mg, 1.2 mmol) was added to the solution and stirring was continued at room temperature for 1 h. The solvent was evaporated at <50° C., and the residue was taken up in 10 ml of water and the aqueous solution was adjusted to pH 2 with 4 M hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and dried to give 274 mg (77%) of crude title compound; 1H-NMR (DMSO-d6): δ1.12 (d, 6H, 2×CH3), 2.28 (s, 3H, COCH3), 4.21 (m, 1H, NCH), 7.15 (s, 1H, H-4), 8.34 (br d, 1H, NH), 10.26 (s, 1H, NH).

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