Synthesis
Example 6 - Preparation of N,N'-bis(p-toluenesulfonyl)hydrazine: To a solution of dichloromethane (50 mL) containing p-toluenesulfonylhydrazine (9.32 g, 50 mmol) and p-toluenesulfonyl chloride (14.3 g, 75 mmol) was added pyridine (6 mL, 75 mmol). The reaction mixture was stirred at room temperature for 1.5 hours. Subsequently, ether (200 mL) and water (100 mL) were added and stirring was continued at 0°C for 15 minutes. After completion of the reaction, the mixture was filtered and the solid product was washed with ether. Finally, purification by recrystallization from methanol afforded N,N'-bis(p-toluenesulfonyl)hydrazine as a white solid (11.5 g, 68% yield).
References
[1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1407 - 1413
[2] Chemical Communications, 2017, vol. 53, # 54, p. 7485 - 7488
[3] Organic Letters, 2007, vol. 9, # 16, p. 3195 - 3197
[4] Chemical Communications, 2018, vol. 54, # 28, p. 3516 - 3519
[5] Liebigs Annalen der Chemie, 1991, # 10, p. 983 - 986