Phenylhydrazine → HCID 13064192, compound

HRID 1388727Notes

Reaction equation

HRID 1388727 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH3:16])[CH:12]=[CH:13][C:14]#[N:15]>C(O)C>[NH2:15][C:14]1[CH2:13][CH:12]([CH:11]([CH3:16])[CH3:10])[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 5360545SodiumHCID 54535780HCID 54535780, compound

Product 1

HCID 13064192HCID 13064192, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.31 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 6.3 g. of phenylhydrazine is added followed by 5.5 g. of 4-methyl-2-pentenonitrile. The reaction mixture is refluxed for 16 hours. The solvent is removed in vacuo, water is added to the residue and the mixture is extracted with dichloromethane. The extract is dried over anhydrous magnesium sulfate and evaporated to give a gum. The gum is chromatographed on a column containing 400 g. of a synthetic magnesium silicate absorbent. The column is eluted first with protions of 21/2% acetone-hexane and 5% acetone-hexane to remove exteraneous colored material, then with portions of 25% and 10% acetone-hexane to remove the product. The product cuts are evaporated to give 2.7 g. of a dark gum which solidifies on standing. This material is recrystallized twice from ether-hexane to give 1.7 g. of the product of the Example as tan crystals, m.p. 115°-117° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customThe solvent is removed in vacuo, water
  3. additionis added to the residue
  4. extractionthe mixture is extracted with dichloromethane
  5. dry with materialThe extract is dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto give a gum
  8. customThe gum is chromatographed on a column
  9. additioncontaining 400 g
  10. washThe column is eluted first with protions of 21/2% acetone-hexane and 5% acetone-hexane
  11. customto remove exteraneous colored material
  12. customwith portions of 25% and 10% acetone-hexane to remove the product
  13. customThe product cuts are evaporated
  14. customto give 2.7 g
  15. customThis material is recrystallized twice from ether-hexane
  16. customto give 1.7 g

Sources & evidence

ORD record
ord-ac6e49ac7a7746399e7a3f4bf4c79c2d
Source dataset
uspto-grants-1984_02
Patent number
US04432991

Reaction notes

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