Phenylhydrazine → HCID 15580664, compound

HRID 2198973Notes

Reaction equation

HRID 2198973 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](#[N:14])[C:11]([CH3:13])=[CH2:12]>C(O)C>[NH2:14][C:10]1[CH:11]([CH3:13])[CH2:12][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 31368MethacrylonitrileHCID 5360545Sodium

Product 1

HCID 15580664HCID 15580664, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.0 g. amount of sodium metal is dissolved in 200 ml. of absolute ethanol, then 37.4 g. of phenylhydrazine is added followed in 10 minutes by 20.1 g. of methacrylonitrile. The reaction mixture is refluxed for 4 hours then is evaporated to near dryness in vacuo. Water is added to the residue to separate an oil. The oil crystallizes on standing. The solid is dissolved in dichloromethane. The solution is passed through a short column of a hydrous magnesium silicate. The column effluent is evaporated to give an oil. The oil is crystallized from acetone-hexane then is recrystallized from the same solvent pair to give 20.88 g. of the desired product as colorless crystals, m.p. 83°-84° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customthen is evaporated
  3. additionWater is added to the residue
  4. customto separate an oil
  5. customThe oil crystallizes on standing
  6. dissolutionThe solid is dissolved in dichloromethane
  7. customThe column effluent is evaporated
  8. customto give an oil
  9. customThe oil is crystallized from acetone-hexane
  10. customthen is recrystallized from the same solvent pair
  11. customto give 20.88 g

Sources & evidence

ORD record
ord-8c9477743467421e8c896ed5531a14f8
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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