3-Hydroxy-N-(4-Methoxybenzyl)-4-Nitro-N-(Thiazol-2-Yl)Benzenesulfonamide → HCID 89761412, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence