Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)- → 2,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2,3,5-trichloro-N-(2-hydroxyimino-ethyl)-benzamide (0.85 g, 3.0 mmol ) in MeOH (50 mL) under an argon atmosphere at 0° C. was added methyl orange (trace) followed by a saturated solution of MeOH/HCl until a persistent red color was observed. Sodium cyanoborohydride (0.23 g, 3.65 mmol) was dissolved in MeOH (5 mL) was added sequentially with saturated MeOH/HCl over 0.5 h. The reaction mixture was stirred an additional 1 h and the MeOH was removed in vacuo. The residue was basidified with 10% NaOH and extracted (4×25 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were washed with brine, were dried (NaHCO3) and were concentrated. The residue was diluted with ether/MeOH (9:1) and the precipitate was collected to provide the title compound (0.27 g, 32%) as a white solid. ESMS: M+H=283.

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