Tetrahydrofuran → 1,2-Bis(phenylmethyl) 1,2-hydrazinedicarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of sodium hydroxide (2.50 kg, 62.5 mol) in water (40 L) was charged into an 100 L reactor. Hydrazine hydrate (2.00 kg, 40 mol) and THF (8 L) were added into the above solution. The mixture solution was cooled at 0° C. A pre-prepared solution of Cbz-Cl (13.60 kg CbzCl, 61.99 mol) in 2 L THF was added dropwise to the solution while maintaining the temperature at 0° C. The reaction was allowed to stir for an additional 4 h and a solid precipitated from the solution. The solid was collected by filtration, which was suspended in toluene (5 L). The suspended solution was heated at 80° C., which became clear. The water in the crude product was removed completely under reflux using a Dean-Stark apparatus. The resulting solution was cooled to room temperature and the product precipitated. The product was obtained after filtration to afford bis(phenylmethyl) 1,2-hydrazinedicarboxylate (7.8 Kg, 26 mol, 65%) as a white solid.

Provenance & Evidence