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

Participants

Reaction Steps

Using General Procedure 1: 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (4.9 g, 32.6 mmol), 2,4-dinitro-benzenesulfonyl chloride (9.8 g, 36.8 mmol), pyridine (18 mL), methylene chloride (100 ml), 0° C.-rt, 0/N. Purification: precipitation from hot H2O. The title compound was recrystallized from ethyl acetate as a light-orange solid (9.5 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.0 (s, 1H), 9.27 (s, 1H), 8.88 (d, Hz, 1H), 8.58 (dd, J=2.2, 8.6 Hz, 1H), 8.17 (d, J=8.6 Hz, 1H), 7.51 (d, Hz, 1H), 7.34 (d, J=8.3 Hz, 1H), (dd, J=1.9, 8.3 Hz, 1H), 4.91 (s, 2H); MS (ESI) m/z=378 (M−1, negative).

Provenance & Evidence