1,1'-Carbonyldiimidazole → (E)-1-(2-nitrocinnamyl)-3-(4-pyridyl)-2-imidazolidinone

HRID 476998Notes

Reaction equation

HRID 476998 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1/[CH:6]=[CH:7]/[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)([O-:3])=[O:2].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCCC1.C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1/[CH:6]=[CH:7]/[CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:23]1=[O:24])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14834211(E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethylenediamine

Product 1

HCID 14834212(E)-1-(2-nitrocinnamyl)-3-(4-pyridyl)-2-imidazolidinoneYield 56.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.33 g of (E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethylenediamine dissovled in a mixture of 50 ml of tetrahydrofuran and 50 ml of chloroform was added 1.52 g of carbonyldiimidazole at 0° C. The mixture was stirred at room temperature for 40 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with chloroform. The chloroform layer was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol=3:1) and recrystallized from a mixture of isopropanol and methanol to give 1.44 g of (E)-1-(2-nitrocinnamyl)-3-(4-pyridyl)-2-imidazolidinone.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol=3:1)
  7. customrecrystallized from a mixture of isopropanol and methanol

Sources & evidence

ORD record
ord-2237052f4b014ba79cbcea855a00cea6
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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