1-iodo-3-isothiocyanatobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(3-(4-aminophenyl)thioureido)benzenesulfonamide (0.322 g, 1.0 mmol) in acetonitrile was added 1-iodo-3-isothiocyanatobenzene (0.261 g, 1.0 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and water was added into the crude reaction mixture. The precipitate which formed was filtered, and dried to afford the title product as a white solid (0.452 g, 78%). 1H NMR (400 MHz, DMSO) δ 10.05 (s, 1H), 10.02 (s, 1H), 9.90 (s, 1H), 9.81 (s, 1H), 7.94 (t, J=1.8 Hz, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.68 (d, J=8.8 Hz, 2H), 7.48-7.41 (m, 5H), 7.12 (t, J=8.0 Hz, 1H); MS (ESI), 584 (M+H)+. The solvent was evaporated under reduced pressure and water was added into the crude reaction mixture The precipitate which formed was filtered dried

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-iodo-3-isothiocyanatobenzene (0.13 g, 0.50 mmol) in acetonitrile (10 mL) was added 5-amino-1,3,4-thiadiazole-2-sulfonamide (0.108 g, 0.50 mmol) and anhydrous K2CO3 (0.40 g). The mixture was stirred at 75° C. for 4 hrs. Solvent was evaporated and diluted with water. The precipitated solid was filtered and dried over vacuum to give desired compound (99 mg, 45%) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.99 (brs, 1H), 8.24 (brs, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.69 (t, J=1.8 Hz, 1H), 7.35 (m, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.02 (s, 2H). Solvent was evaporated diluted with water The precipitated solid was filtered dried over vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Pipemidic acid (40 mg, 0.133 mmol) and 3-iodophenyl isothiocyanate (29 mg, 0.111 mmol) were used. Purification on silica yielded compound 29 in Table 1, below (57 mg, 90%). 1H NMR (250 MHz, CDCl3) δ 9.33 (s, 1H), 8.73 (s, 1H), 7.66-7.64 (m, 1H), 7.54-7.51 (m, 1H), 7.40-7.24 (m, 1H), 7.12-7.06 (m, 1H), 4.48-4.31 (m, 2H), 4.27-3.93 (m, 8H), 1.34-1.17 (m, 3H) ppm. Purification on silica yielded compound 29 in Table 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Pipemidic acid (40 mg, 0.133 mmol) and 3-iodophenyl isothiocyanate (29 mg, 0.111 mmol) were used. Purification on silica yielded compound 29 in Table 1, below (57 mg, 90%). 1H NMR (250 MHz, CDCl3) δ 9.33 (s, 1H), 8.73 (s, 1H), 7.66-7.64 (m, 1H), 7.54-7.51 (m, 1H), 7.40-7.24 (m, 1H), 7.12-7.06 (m, 1H), 4.48-4.31 (m, 2H), 4.27-3.93 (m, 8H), 1.34-1.17 (m, 3H) ppm. Purification on silica yielded compound 29 in Table 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(3-(4-aminophenyl)thioureido)benzenesulfonamide (0.322 g, 1.0 mmol) in acetonitrile was added 1-iodo-3-isothiocyanatobenzene (0.261 g, 1.0 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and water was added into the crude reaction mixture. The precipitate which formed was filtered, and dried to afford the title product as a white solid (0.452 g, 78%). 1H NMR (400 MHz, DMSO) δ 10.05 (s, 1H), 10.02 (s, 1H), 9.90 (s, 1H), 9.81 (s, 1H), 7.94 (t, J=1.8 Hz, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.68 (d, J=8.8 Hz, 2H), 7.48-7.41 (m, 5H), 7.12 (t, J=8.0 Hz, 1H); MS (ESI), 584 (M+H)+. The solvent was evaporated under reduced pressure and water was added into the crude reaction mixture The precipitate which formed was filtered dried

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-iodo-3-isothiocyanatobenzene (0.13 g, 0.50 mmol) in acetonitrile (10 mL) was added 5-amino-1,3,4-thiadiazole-2-sulfonamide (0.108 g, 0.50 mmol) and anhydrous K2CO3 (0.40 g). The mixture was stirred at 75° C. for 4 hrs. Solvent was evaporated and diluted with water. The precipitated solid was filtered and dried over vacuum to give desired compound (99 mg, 45%) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.99 (brs, 1H), 8.24 (brs, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.69 (t, J=1.8 Hz, 1H), 7.35 (m, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.02 (s, 2H). Solvent was evaporated diluted with water The precipitated solid was filtered dried over vacuum

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-iodo-3-isothiocyanatobenzene (0.13 g, 0.50 mmol) in acetonitrile (10 mL) was added 5-amino-1,3,4-thiadiazole-2-sulfonamide (0.108 g, 0.50 mmol) and anhydrous K2CO3 (0.40 g). The mixture was stirred at 75° C. for 4 hrs. Solvent was evaporated and diluted with water. The precipitated solid was filtered and dried over vacuum to give desired compound (99 mg, 45%) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.99 (brs, 1H), 8.24 (brs, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.69 (t, J=1.8 Hz, 1H), 7.35 (m, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.02 (s, 2H). Solvent was evaporated diluted with water The precipitated solid was filtered dried over vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Pipemidic acid (40 mg, 0.133 mmol) and 3-iodophenyl isothiocyanate (29 mg, 0.111 mmol) were used. Purification on silica yielded compound 29 in Table 1, below (57 mg, 90%). 1H NMR (250 MHz, CDCl3) δ 9.33 (s, 1H), 8.73 (s, 1H), 7.66-7.64 (m, 1H), 7.54-7.51 (m, 1H), 7.40-7.24 (m, 1H), 7.12-7.06 (m, 1H), 4.48-4.31 (m, 2H), 4.27-3.93 (m, 8H), 1.34-1.17 (m, 3H) ppm. Purification on silica yielded compound 29 in Table 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(3-(4-aminophenyl)thioureido)benzenesulfonamide (0.322 g, 1.0 mmol) in acetonitrile was added 1-iodo-3-isothiocyanatobenzene (0.261 g, 1.0 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and water was added into the crude reaction mixture. The precipitate which formed was filtered, and dried to afford the title product as a white solid (0.452 g, 78%). 1H NMR (400 MHz, DMSO) δ 10.05 (s, 1H), 10.02 (s, 1H), 9.90 (s, 1H), 9.81 (s, 1H), 7.94 (t, J=1.8 Hz, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.68 (d, J=8.8 Hz, 2H), 7.48-7.41 (m, 5H), 7.12 (t, J=8.0 Hz, 1H); MS (ESI), 584 (M+H)+. The solvent was evaporated under reduced pressure and water was added into the crude reaction mixture The precipitate which formed was filtered dried

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-iodo-3-isothiocyanatobenzene (0.13 g, 0.50 mmol) in acetonitrile (10 mL) was added 5-amino-1,3,4-thiadiazole-2-sulfonamide (0.108 g, 0.50 mmol) and anhydrous K2CO3 (0.40 g). The mixture was stirred at 75° C. for 4 hrs. Solvent was evaporated and diluted with water. The precipitated solid was filtered and dried over vacuum to give desired compound (99 mg, 45%) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.99 (brs, 1H), 8.24 (brs, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.69 (t, J=1.8 Hz, 1H), 7.35 (m, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.02 (s, 2H). Solvent was evaporated diluted with water The precipitated solid was filtered dried over vacuum