Ethylenediamine → HCID 21940017, compound

HRID 1242937Notes

Reaction equation

HRID 1242937 reaction equation
[ClH:1].C(O)C.[C:5](/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[O:17])=[CH:11][CH:10]=1)#[N:6].[CH2:30](N)[CH2:31][NH2:32].C(=O)([O-])O.[Na+]>C(O)C>[ClH:1].[NH:6]1[CH2:30][CH2:31][N:32]=[C:5]1/[CH:7]=[CH:8]/[C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[O:17])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 21939849HCID 21939849, compound

Product 1

HCID 21940017HCID 21940017, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.1 N Hydrogen chloride-ethanol solution (30 ml) was added to an ethanol suspension of N-[4-[(E)-2-cyanoethenyl]phenyl][1,1′-biphenyl]-4-carboxamide (250 mg, 0.771 mmol) obtained in Reference Example under room temperature, which was stirred for 16 hours. After the solvent was distilled out under reduced pressure, ethanol was again added to the residue, and then ethylenediamine (0.155 ml, 2.31 mmol) was added at room temperature, which was stirred for 16 hours. Sodium hydrogencarbonate solution was added to the reaction mixture, and the precipitated crude product was washed with water and chloroform. This product was dissolved in methanol. 1 N Hydrochloric acid (4 ml) was added to the solution, and the solvent was distilled out under reduced pressure. Small amount of water was added to the resulting residue, to give the titled compound (124 mg) as a colorless powder.

Workup

  1. customobtained in Reference Example under room temperature
  2. distillationAfter the solvent was distilled out under reduced pressure, ethanol
  3. additionwas again added to the residue
  4. stirringwhich was stirred for 16 hours
  5. customthe precipitated crude product
  6. washwas washed with water and chloroform
  7. dissolutionThis product was dissolved in methanol
  8. addition1 N Hydrochloric acid (4 ml) was added to the solution
  9. distillationthe solvent was distilled out under reduced pressure
  10. additionSmall amount of water was added to the resulting residue

Sources & evidence

ORD record
ord-f9b6fa84e83b434981c7de4b63e731e2
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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