Potassium Carbonate → 3-chloro-2-methyl-N-(2-methyl-1,3-benzothiazol-5-yl)benzenesulfonamide

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Reaction Steps

To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330.

Provenance & Evidence