Acrylonitrile → HCID 12551447, compound

HRID 2198977Notes

Reaction equation

HRID 2198977 reaction equation
[Na].Cl.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[C:12](#[N:15])[CH:13]=[CH2:14]>C(O)C>[NH2:15][C:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[N:11]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 5360545Sodium

Product 1

HCID 12551447HCID 12551447, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.8 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 15.86 g. of p-methylphenylhydrazine hydrochloride is added followed in 5 minutes by 5.5 g. of acrylonitrile. The reaction mixture is refluxed for 18 hours, then is evaporated to dryness in vacuo. Water is added and the separated solid is collected by filtration. The solid is dissolved in dichloromethane and passed through a short column of a hydrous magnesium silicate. The effluent is refluxed with the gradual addition of hexane to separate a crystalline product. The entire crystallization step is repeated to give 3.4 g. of the product of the Example as colorless plates, m.p. 142°-143° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. customis evaporated to dryness in vacuo
  3. additionWater is added
  4. filtrationthe separated solid is collected by filtration
  5. dissolutionThe solid is dissolved in dichloromethane
  6. temperatureThe effluent is refluxed with the gradual addition of hexane
  7. customto separate a crystalline product
  8. customThe entire crystallization step
  9. customto give 3.4 g

Sources & evidence

ORD record
ord-f462a4af4793447f928104097ab77697
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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