Synthesis
At room temperature, 115 g (0.6 mol) of p-toluenesulfonyl chloride was dissolved in 250 ml of pyridine. Pyridine solution (30 ml) containing diethylenetriamine (21.5 ml, 0.2 mol) was added slowly and dropwise. The reaction mixture was stirred continuously at 50°C for 90 min and subsequently transferred to a conical flask under warm condition. After the mixture was cooled to room temperature, 200 ml of water was added. The mixture was stirred overnight at room temperature and subsequently cooled in an ice bath for 2 hours. The orange solid formed was collected by filtration and washed with 95% ethanol pre-cooled to 0°C. Finally, the product was dried under vacuum by rotary evaporator at 40°C to afford the target compound N,N,N-tris(p-toluenesulfonyl)diethylenetriamine (92 g, 81% yield) in light yellow solid form.
References
[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 22, p. 3651 - 3656
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 3, p. 397 - 406
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 2, p. 372 - 375
[4] Dalton Transactions, 2016, vol. 45, # 23, p. 9412 - 9418
[5] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17366 - 17369
