反应详情

温度

70 °C

To a solution of 3-hydroxy-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide (9 g, 21.3 mmol) in AcOH (70 ml) was added Fe-powder (5.98 g, 106.0 mmol, Qualigens) and the resulting suspension was stirred at 70° C. for 2 h. The mixture was cooled to 25° C. The organic compound was extracted with EtOAc, washed with saturated aqueous solution of NaHCO3, dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel chromatography using a gradient of 0-50% EtOAc in hexanes as eluent to afford 5.5 g of 4-amino-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide (INTERMEDIATE AD) as off white solid in 66.2% yield. 1H-NMR (400 MHz, DMSO): δ 9.82 (s, 1H), 7.37 (s, 1H), 7.29 (m, 1H), 7.21-7.25 (m, 2H), 7.08-7.09 (dd, 1H), 7.06 (s, 1H), 6.84 (d, J=8.8 Hz, 2H), 6.62 (d, J=8.4 Hz, 1H), 5.67 (s, 2H), 4.91 (s, 2H), 3.70 (s, 3H); m/z (ESI, positive ion) 392.1 (M+H).

1. temperatureThe mixture was cooled to 25° C
2. extractionThe organic compound was extracted with EtOAc
3. washwashed with saturated aqueous solution of NaHCO3
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customThe resulting residue was purified by silica gel chromatography