Acetic Acid → HCID 89761746, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-bromo-4-nitrophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.025 g, 0.040 mmol) was dissolved in THF (0.135 mL) and acetic acid (0.127 mL, 2.227 mmol), and iron (0.023 g, 0.405 mmol) was added. The flask was sealed and heated to 70° C. for 1 hour. The reaction was cooled to rt, diluted with THF, and filtered through Celite® (diatomaceous earth), washing well with THF. The filtrate was concentrated, and partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The layers were separated, and the aqueous was then extracted (×2) with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to yield 4-(4-amino-2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a light brown solid. The material was carried forward without further purification. m/z (ESI) 587.1 (M+H)+.

Provenance & Evidence