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

HRID 1396843Notes

Reaction equation

HRID 1396843 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][NH2:13].[C:14](=[O:17])([O-])[O-:15].[Na+].[Na+]>CO.O>[NH:12]([C:14]([O:15][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:17])[NH:13][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 2205541,2-Bis(phenylmethyl) 1,2-hydrazinedicarboxylateYield 71.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. filtrationbefore being filtered under suction
  2. customisolating a solid which
  3. washwas washed with ice water
  4. concentrationThe resulting filtrate was concentrated
  5. customto remove the methanol
  6. customyielding a small quantity of solid material
  7. filtrationupon filtration
  8. washThis solid material was again washed with ice water
  9. customThe combined solids were recrystallized from straight toluene
  10. customThe resulting white solid was dried in a vacuum oven at 60° C. for 5 hours

Sources & evidence

ORD record
ord-363b35388e524420afad38802d4998c2
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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