反应详情

A mixture of 5-bromo-1,3-benzothiazole-2-thiol (3.0 g, 12.19 mmol), dry THF (44 mL), iodomethane (0.80 mL, 12.80 mmol), KOH (0.68 g, 12.19 mmol), and tetra-n-butylammonium bromide (0.39 g, 1.2 mmol) was stirred at rt overnight. The reaction mixture was diluted with EtOAc (100 mL) and washed with saturated, aqueous Na2CO3 (50 mL). The organic layer was dried over MgSO4 and then concentrated. The crude material was purified by ISCO® chromatography using 1-2% EtOAc in hexane to obtain the desired product (2.4 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ 8.02 (s, 1H), 8.0 (d, 1H), 7.51 (d, 1H), 2.79 (s, 3H); LC-MS m/z[M+H]+ 260.3 & 262.2, RT 3.82 min.

1. washwashed with saturated, aqueous Na2CO3 (50 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. concentrationconcentrated
4. customThe crude material was purified by ISCO® chromatography