3-Phenylprop-2-enenitrile → HCID 13064195, compound

HRID 2198985Notes

Reaction equation

HRID 2198985 reaction equation
[Na].Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.[C:13](#[N:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[NH2:22][C:13]1[CH2:14][CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[N:12]=1

Participants

5

Reactant 3

HCID 746673-Phenylprop-2-enenitrileHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 5360545Sodium

Product 1

HCID 13064195HCID 13064195, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 4.42 g. amount of sodium metal is dissolved in 300 ml. of absolute ethanol, then 27.8 g. of p-methoxyphenylhydrazine hydrochloride is added followed in 5 minutes by 20.64 g. of cinnamonitrile. The reaction mixture is refluxed for 7 hours, then is evaporated to dryness in vacuo. Water is added to the residue to give a sludge. The mixture is filtered and the residue is evaporated to dryness. The solid is dissolved in dichloromethane and crystallized as described in Example 16 to give 4.75 g. of the desired product as colorless needles, m.p. 163.5°-166° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 7 hours
  2. customis evaporated to dryness in vacuo
  3. additionWater is added to the residue
  4. customto give a sludge
  5. filtrationThe mixture is filtered
  6. customthe residue is evaporated to dryness
  7. dissolutionThe solid is dissolved in dichloromethane
  8. customcrystallized
  9. customto give 4.75 g

Sources & evidence

ORD record
ord-072f316e2d8d4cdf92b7e9d12782336b
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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