Ethylenediamine → 4-Cyano-2'-nitrodiphenyl

HRID 258059Notes

Reaction equation

HRID 258059 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)([O-:3])=[O:2].[Cu](C#N)[C:18]#[N:19].CN(C=O)C.C(N)CN>O.CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:18]#[N:19])=[CH:12][CH:11]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 218576474'-Bromo-2-nitrobiphenylHCID 178418260HCID 178418260, compound

Product 1

HCID 118511144-Cyano-2'-nitrodiphenyl

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

20 g (7.19 10-2 moles) of 4 nitro 4'bromobiphenyl, 11.6 of copper cyanide and 120 ml of DMF are placed in a 250 ml receptacle with a magnetic agitator. The mixture is refluxed for 5 h 30. It is then allowed to cool, acetone is added and the reaction medium is poured into 2 liters of water containing 2 g of ethylene diamine. A precipitate is formed. The solid is filtered out then washed in water and hexane. This raw product is redissolved in chloroform. The organic phase is dried on MgSO4, filtered and evaporated till dry. The solid obtained is recrystallized in an ethanol-chloroform mixture. This provides 13.16 g of product, yield ρ=81.7%, melting point=195° C.

Workup

  1. temperatureThe mixture is refluxed for 5 h 30
  2. temperatureto cool
  3. customA precipitate is formed
  4. filtrationThe solid is filtered
  5. washout then washed in water
  6. dissolutionThis raw product is redissolved in chloroform
  7. customThe organic phase is dried on MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customtill dry
  11. customThe solid obtained
  12. customis recrystallized in an ethanol-chloroform mixture

Sources & evidence

ORD record
ord-1ad01d141bc0437d83f2cc676e142a63
Source dataset
uspto-grants-1993_11
Patent number
US05264512

Reaction notes

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