Ethanol → HCID 13064196, compound

HRID 2198986Notes

Reaction equation

HRID 2198986 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C/[C:11](=[CH:14]\[CH3:15])/[C:12]#[N:13].[CH2:16](O)C>>[NH2:13][C:12]1[CH2:11][CH:14]([CH2:15][CH3:16])[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 7516PhenylhydrazineHCID 5355732(E)-2-Methyl-2-butenenitrileHCID 5360545Sodium

Product 1

HCID 13064196HCID 13064196, compound

Procedure

A 0.23 g. amount of sodium metal is dissolved in 75.0 ml. of absolute ethanol, then 10.8 g. of phenylhydrazine is added, followed in 5 minutes by 3.6 g. of α-methylcrotononitrile. The reaction mixture is refluxed for 18 hours, then is evaporated to dryness in vacuo. Water is added to give a gum which solidifies on standing for 16 hours. The solid is collected and dissolved in dichloromethane. The procedure of Example 15 is continued to give 1.6 g. of the desired product as light yellow crystals, m.p. 123°-125° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. customis evaporated to dryness in vacuo
  3. additionWater is added
  4. customto give a gum which
  5. waiton standing for 16 hours
  6. customThe solid is collected
  7. dissolutiondissolved in dichloromethane
  8. customto give 1.6 g

Sources & evidence

ORD record
ord-0eea72748caa4716a5b69ee47561b1a3
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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