2-Nitrobenzenesulfonyl chloride → HCID 69288393, compound

Participants

Reaction Steps

2-Azabicyclo[2.2.1]hept-5-ene (52.5 g, 54 mmole), prepared as described in (J Am Chem. Soc., (1985) 107, 1768), 2-nitrobenzenesulfonyl chloride (119.6, 54 mmole), and triethylamine (75 mL, 0.54 mmole) were combined in methylene chloride (500 mL) under a nitrogen atmosphere and stirred for 16 hours. The reaction mixture was quenched with water (500 mL) and the phases separated. The organic phase was washed with 2M HCl (5×100 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (chloroform then hexane:EtOAc 95:5 to 8:2) to provide the title compound (23 g, 23% yield). MS (DCI/NH3) m/e 281 (M+H)+, 298 (M+NH4)+.

Provenance & Evidence