Sodium ethoxide → HCID 54274638, compound

HRID 1378381Notes

Reaction equation

HRID 1378381 reaction equation
[O-]CC.[Na+].[Br-].[CH3:6][N:7]([CH3:37])[C:8]1[C:9]([N+:34]([O-:36])=[O:35])=[C:10]([CH:31]=[CH:32][CH:33]=1)[CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:38]1([C:44]2[N:45]=[CH:46][N:47]([CH2:49][CH2:50][CH:51]=O)[CH:48]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[N+:34]([C:9]1[C:10]([CH:11]=[CH:51][CH2:50][CH2:49][N:47]2[CH:48]=[C:44]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:45]=[CH:46]2)=[CH:31][CH:32]=[CH:33][C:8]=1[N:7]([CH3:6])[CH3:37])([O-:36])=[O:35]

Participants

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 10029681HCID 10029681, compoundHCID 10679531HCID 10679531, compound

Product 1

HCID 54274638HCID 54274638, compoundYield 142.2%

Procedure

An ethanolic solution of 900 mg of sodium ethoxide was dropped into an ethanolic solution containing 6.88 g of 3-dimethylamino-2-nitrobenzyl-triphenylphosphonium bromide and 3.22 g of 3-(4-phenyl-1H-imidazol-1-yl)propionaldehyde. The obtained solution was heated under reflux for 2 hours to conduct a reaction. After the completion of the reaction, the reaction mixture was freed from the solvent by distillation and extracted With 2N NaOH. The aqueous layer was made acidic again with 1N HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of common salt, dried over magnesium sulfate and distilled to remove the solvent. The obtained oily substance was purified by silica gel chromatography to give 6.80 g of 2-nitro-3-[4-(4-phenyl-1H-imidazol-1-yl)butenyl]-N,N-dimethylaniline. 680 mg of 10% Pd-C was added to a solution of the product in ethyl acetate to conduct catalytic reduction in a hydrogen stream. Thus, 2-dimethylamino-6-[4-(4-phenyl-1H-imidazol-1-yl) butyl]aniline was obtained as an oily substance. This substance was dissolved in chloroform to give a solution. 1.1 g of butyl isocyanate was dropped into the solution. The obtained mixture was heated under reflux for two hours to conduct a reaction. After the completion of the reaction, the reaction mixture was concentrated to precipitate a crystal. This crystal was recrystallized from an ethyl acetate/hexane mixture. Thus, 4.51 g of the title compound was obtained.

Workup

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 2 hours
  3. customa reaction
  4. customAfter the completion of the reaction
  5. distillationthe reaction mixture was freed from the solvent by distillation
  6. extractionextracted With 2N NaOH
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with a saturated aqueous solution of common salt
  9. dry with materialdried over magnesium sulfate
  10. distillationdistilled
  11. customto remove the solvent
  12. customThe obtained oily substance was purified by silica gel chromatography

Sources & evidence

ORD record
ord-89410435b1054dadbcbf40d9a8459215
Source dataset
uspto-grants-1997_09
Patent number
US05668136

Reaction notes

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