4-Nitrobenzenesulfonyl chloride → HCID 22997215, compound

Participants

Reaction Steps

4-tetrahydropyranoxyhydroxylamine (33.2 mmol, 3.77 g) and 4-nitrobenzenesulfonylchloride (38.6 mmol, 8.56 g) were combined in anhydrous THF (100 mL) with diisopropylethylamine (69.3 mmol, 11.2 mL). The reaction was stirred at room temperature for 48 hours. Hydrazine (2 mL) was injected to the stirring solution to break-up the bisarylsulfonamide dimer biproduct. The reaction was stirred for an additional 24 hours. The reaction was diluted in ethyl acetate, washed in brine, filtered to remove insoluble solids and concentrated. The crude was purified by crystallization from hot ethyl acetate to provide 3.5 g (36%) of white crystals. Rf=0.3 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 8.42 (2H,d), 8.13 (2H,d), 6.93 (1H,s), 4.27 (1H,m), 3.91 (2H,m), 3.45 (2H,m), 2.02 (2H,m), 1.61 (2H,m).

Provenance & Evidence