Dimethylamine → 4-iodo-N,N-dimethylbenzenesulfonamide

Participants

Reaction Steps

Dimethylamine (100 mL of 2.0 M THF solution; 200 mmol) was added to a solution of pipsyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of N,N-dimethylaminopyridine (15 mg). The reaction was stirred under N2 for two days while it warmed from 0° C. to room temperature. The reaction solution was poured into 1.2 liter of water. The desired product was precipitated out of the H2O/pyridine solution. The solid was collected by filtration and rinsed by H2O (300 mL×2). The solid was dissolved in EtOAc (500 mL). The EtOAc solution was washed by 5% aqueous HCl (300 mL×3), water (300 mL×2) and brine (300 mL×1), dried by Na2SO4 and concentrated to give 4-iodo-N,N-dimethylbenzenesulfonamide (49.46 g; 88%) as white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H).

Provenance & Evidence