1,3-Benzothiazole-4-sulfonyl Chloride synthesis

Yield:149575-65-5 218 mg

Reaction Conditions:

with chlorosulfonic acid at 0 - 105;

Steps:

6.24-1.A Benzo[d]thiazole-4-sulfonyl chloride (24B)

Benzo[d]thiazole (lg, 7.45 mol) was added dropwise to chlorosulfonic acid (5.5 mmol) at 0°C. After the addition was complete, the mixture was stirred at room temperature for 0.5 h and then heated at 105°C and stirred overnight. The resulting mixture was cooled to -10°C and quenched by pouring on crushed ice slowly. The resulting mixture was extracted with EtOAc (100 mL x 2). The combined organic phase was washed with brine, dried over anhy. Na₂S0₄ and concentrated in vacuo. Column chromatography (15% PE/EtOAc) afforded 218 mg of title compound. 1H NMR (CHLOROFORM-d) δ: 9.41 (s, 1H), 8.41 (dd, J = 8.1, 1.0 Hz, 1H), 8.29 (dd, J = 7.7, 1.1 Hz, 1H), 7.68 (t, J = 7.9 Hz, 1H). LC-MS: m/z 234.7 (M+H)⁺

References:

WO2014/139144,2014,A1 Location in patent:Page/Page column 181; 182; 218