Hydrazine → HCID 178425010, compound

HRID 324428Notes

Reaction equation

HRID 324428 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)=O)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:22][NH2:23]>O1CCOCC1.O1CCCC1>[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)=[N:22][NH2:23])#[N:2]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 24819Phosphorus pentachlorideHCID 22003626HCID 22003626, compound

Product 1

HCID 178425010HCID 178425010, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from step (vii) (35.68 g) and phosphorus pentachloride (36.86 g) was stirred under a water-aspirator vacuum and heated at 100° C. giving rise to a yellow oil. The oil was further stirred at 100° C. under vacuum for a further 30 min. The boiling phosphorus oxychloride liberated was collected by distillation to leave a dark brown oil which was cooled to room temperature and dissolved in dry 1,4-dioxane (50 ml). This solution was transferred rapidly via cannula to a stirring solution of hydrazine in tetrahydrofuran (1.0M, 882 ml) under nitrogen at room temperature. An exotherm was produced raising the reaction temperature to ˜40° C. The resultant opaque yellow solution was further stirred for 16 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was collected, dried over magnesium sulphate and solvent removed under reduced pressure to give the subtitle product as a red oil (34.7 g). This was not purified but used directly in the next step

Workup

  1. customgiving rise to a yellow oil
  2. stirringThe oil was further stirred at 100° C. under vacuum for a further 30 min
  3. distillationThe boiling phosphorus oxychloride liberated was collected by distillation
  4. customto leave a dark brown oil which
  5. temperaturewas cooled to room temperature
  6. customAn exotherm was produced
  7. temperatureraising the reaction temperature to ˜40° C
  8. stirringThe resultant opaque yellow solution was further stirred for 16 h
  9. customThe solvent was removed under reduced pressure
  10. customthe residue partitioned between ethyl acetate and water
  11. customThe organic layer was collected
  12. dry with materialdried over magnesium sulphate and solvent
  13. customremoved under reduced pressure

Sources & evidence

ORD record
ord-2957dbe4b1ca4b889904635cbb08aa13
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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