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

Participants

Reaction Steps

Benzyl chloroformate (19.73 mL, 140 mmol) was added dropwise to a solution of hydrazine (2 mL, 63.7 mmol) in methanol (200 mL). Approximately half way through the addition, dropwise addition of a solution of sodium carbonate (14.86 g, 140 mmol) in water (150 mL) commenced. The resulting slurry was stirred for about 45 min before being filtered under suction, isolating a solid which was washed with ice water. The resulting filtrate was concentrated to remove the methanol, yielding a small quantity of solid material upon filtration. This solid material was again washed with ice water. The combined solids were recrystallized from straight toluene. The resulting white solid was dried in a vacuum oven at 60° C. for 5 hours. This yielded bis(phenylmethyl) 1,2-hydrazinedicarboxylate (13.74 g, 45.8 mmol, 71.8% yield) as a white crystalline solid.

Provenance & Evidence