Propylene Carbonate → HCID 86745783, compound

HRID 1534969Notes

Reaction equation

HRID 1534969 reaction equation
O.[NH2:2][NH2:3].[C:4]1(=[O:10])[O:9][CH:7]([CH3:8])[CH2:6][O:5]1.C1(=O)OC(C)C[O:12]1.NN>C1(C)C=CC=CC=1>[C:4]1(=[O:10])[O:9][CH:7]([CH3:8])[CH2:6][O:5]1.[OH2:12].[NH2:2][NH2:3]

Participants

5

Reactant 3

HCID 7924Propylene CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 67744681HCID 67744681, compound

Product 1

HCID 86745783HCID 86745783, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 67.5 g of hydrazine hydrate (1.35 moles), 60 g of toluene and 290 g of propylene carbonate (2.8 moles) was heated to 90° C. for 2 hours. The water in the system was removed by azeotropic distillation with toluene under reduced pressure (water aspirator). The excess propylene carbonate (108 g) was removed by vacuum distillation to afford a mixture of the 1:1 and 2:1 propylene carbonate/hydrazine adducts. By calculation the product was present in an approximately 70/30 ratio on a molar basis and an approximately 55/45 ratio on a weight basis of the 1:1 and 2:1 adducts.

Workup

  1. customThe water in the system was removed by azeotropic distillation with toluene under reduced pressure (water aspirator)
  2. customThe excess propylene carbonate (108 g) was removed by vacuum distillation
  3. customto afford

Sources & evidence

ORD record
ord-376f5b4144944ec0b3c8d8b42e91f10f
Source dataset
uspto-grants-1992_02
Patent number
US05091475

Reaction notes

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