Ethanol → HCID 13064193, compound

HRID 1388729Notes

Reaction equation

HRID 1388729 reaction equation
[Na].C(O)C.[C:5]1([NH:11][NH2:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]([C:19]#[N:20])[CH:14]=[CH:15][CH2:16][CH2:17]C>CCCCCC>[NH2:20][C:19]1[CH2:13][CH:14]([CH2:15][CH2:16][CH3:17])[N:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7516PhenylhydrazineHCID 5360545SodiumHCID 54415427Hept-3-enenitrile

Product 1

HCID 13064193HCID 13064193, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 0.2 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 3.1 g. of phenylhydrazine is added followed by 2.7 g. of 2-hexenecarbonitrile. The reaction mixture is refluxed for 18 hours then is evaporated to dryness in vacuo. The residue is dissolved in dichloromethane. The solution is washed with water, dried over anhydrous magnesium sulfate, filtered through a short column of a hydrous magnesium silicate and evaporated to dryness in vacuo to give a tan gum. Hexane is added and the gum solidifies. The tacky solid is collected and dried. The solid is dissolved in ether and concentrated while adding hexane to give 3.3 g. of the product of the Example as light tan crystals, m.p. 118°-120° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. customthen is evaporated to dryness in vacuo
  3. dissolutionThe residue is dissolved in dichloromethane
  4. washThe solution is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered through a short column of a hydrous magnesium silicate
  7. customevaporated to dryness in vacuo
  8. customto give a tan gum
  9. customThe tacky solid is collected
  10. customdried
  11. dissolutionThe solid is dissolved in ether
  12. concentrationconcentrated
  13. additionwhile adding hexane
  14. customto give 3.3 g

Sources & evidence

ORD record
ord-da7f6fd410bd4402bce0a121d5402b10
Source dataset
uspto-grants-1984_02
Patent number
US04432991

Reaction notes

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