2-Nitrobenzenesulfonyl chloride → HCID 5461210, compound

Participants

Reaction Steps

A solution of propargylamine (2 mL, 29 mmol) and N,N-diisopropylethylamine (10 mL, 57.4 mmol) in methylene chloride (100 mL) was cooled to 0° C. 2-nitrobenzenesulfonyl chloride (6.46 g, 29.2 mmol) was added portionwise. Upon complete addition, the solution was allowed to warm to room temperature and was further stirred at room temperature overnight. The reaction solution was concentrated in vacuo and the residue obtained was directly purified on silica chromatography (20-50% EtOAc/hexane) to afford Intermediate 14 as white solid (5.90 g, 84%). LC-MS: (FA) ES+241; 1H NMR (400 MHz, CDCl3) δ 8.22-8.17 (m, 1H), 7.94-7.89 (m, 1H), 7.79-7.73 (m, 2H), 5.71 (s, 1H), 4.02 (dd, J=5.9, 2.4 Hz, 2H), 1.97 (t, J=2.5 Hz, 1H).

Provenance & Evidence