N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2,4-dinitrobenzenesulfonamide → 2,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Participants

Reaction Steps

To a solution of N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2,4-dinitrobenzenesulfonamide (0.43 g, 1.14 mmol) was added Raney-Ni (100 mg), following by degas and replacement of air with H2. The reaction mixture was hydrogenated at room temperature for 2 hours. Once the reaction was completed (LC/MS), the mixture was filtered through Celite®. The filtrate was concentrated in vacuo to give a gummy material. The crude product was recrystallized in MeOH to give the title compound as an off-white solid (0.32 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (s, 1H), 9.15 (s, 1H), 7.41 (s, 1H), 7.10˜7.18 (m, 3H), 5.72˜5.73 (m, 2H), 5.60 (s, 1H), 5.52 (s, 2H), 4.84 (s, 2H); MS (ESI) m/z=318 (M−1, negative); HPLC purity: 99.6% (MaxPlot 200-400 nm), 99.3% (220 nm).

Provenance & Evidence