4-Nitrobenzenesulfonyl chloride → HCID 3112496, compound

Participants

Reaction Steps

Diisopropylethylamine (9.4 ml, 54.1 mmol) was added in one portion to a stirred solution of methyl isonipecotate (6.78 g, 47.4 mmol) in THF (100 ml) at room temperature. To this mixture was added 4-nitrobenzenesulfonyl chloride (10.0 g, 45.1 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. After this time, the resulting solid precipitate was collected by filtration and washed with cold THF (50 ml) before being dried under to give the title compound (14.8 g, 100% yield) as a white solid. δH (500 MHz, DMSO) 8.45 (2H, d), 8.02 (2H, d), 3.66-3.54 (5H, m), 2.52 (2H, obscured), 2.45-2.36 (1H, m), 1.96-1.88 (2H, m), 1.64-1.52 (2H, m). Tr=1.88 min m/z (ES+) (M+H+) 329.

Provenance & Evidence