Nitrogen → HCID 71129228, compound

HRID 2197279Notes

Reaction equation

HRID 2197279 reaction equation
[N:1]#[N:2].[C:3]([NH:15][NH2:16])(=[O:14])[C:4]1[C:5](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:6]([NH:8][NH2:9])=[O:7].O.NN.NN>O>[C:3]([NH:15][NH2:16])(=[O:14])[C:4]1[C:5](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:6]([NH:8][NH2:9])=[O:7].[NH2:1][NH2:2]

Participants

6

Reactant 4

HCID 947NitrogenHCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 11367556Phthalohydrazide

Product 1

HCID 71129228HCID 71129228, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The general procedure from H. J. Barber et. al. Journal of the Chemical Society, 1948, page 1458 was followed. A 250 mL round bottom flask equipped with a magnetic stir bar and a condenser further attached to a N2 source was charged with 10.0 g (61.7 mmol, available from Aldrich,) phthalhydrazide, 9.57 g (191 mmol, available from Aldrich) hydrazine hydrate, and 60 mL of water. The mixture was heated to 90° C. at which point it became substantially homogeneous, then filtered while warm. The filtrate was added to about 1 L of ethanol then the precipitate was collected by filtration and dried in vacuo at room temperature to afford 9.0 g (46 mmol, 75% yield) of fluffy, white powder. TGA analysis showed 15.7 wt % loss by 150° C. (16.5% is theoretical loss of hydrazine).

Workup

  1. customA 250 mL round bottom flask equipped with a magnetic stir bar and a condenser
  2. filtrationfiltered
  3. temperaturewhile warm
  4. additionThe filtrate was added to about 1 L of ethanol
  5. filtrationthe precipitate was collected by filtration
  6. customdried in vacuo at room temperature
  7. customto afford 9.0 g (46 mmol, 75% yield) of fluffy, white powder
  8. customby 150° C.

Sources & evidence

ORD record
ord-bce113488458423daef15170d5bb26f0
Source dataset
uspto-grants-2012_12
Patent number
US08338542B1

Reaction notes

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