Sodium ethoxide → HCID 67725831, compound

HRID 1378383Notes

Reaction equation

HRID 1378383 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>>[C:38]1([C:44]2[N:45]=[CH:46][N:47]([CH2:49][CH2:50]/[CH:51]=[CH:11]\[C:10]3[C:9]([N+:34]([O-:36])=[O:35])=[C:8]([CH:33]=[CH:32][CH:31]=3)[N:7]([CH3:6])[CH3:37])[CH:48]=2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 3

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

Product 1

HCID 67725831HCID 67725831, compoundYield 48.7%

Procedure

An ethanolic solution of 90 mg of sodium ethoxide was dropped into an ethanolic solution containing 650 mg of 3-dimethylamino-2-nitrobenzyltriphenylphosphonium bromide and 320 mg 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 mixture was distilled to remove the solvent. The residue was extracted with 2N NaOH and the obtained 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 which is a mixture of cis- and trans-isomers was purified by silica gel chromatography to give 220 mg of 3-[4-(4-phenyl-1H-imidazol-1-yl)-1-cis-butenyl]-2-nitro-N,N-dimethylaniline. 430 mg of zinc was added to a solution of this product in acetic acid to give 2-dimethylamino-6-[4-(4-phenyl-1H-imidazol-1-yl)-1-Cis-butenyl]aniline as an oily substance. This oily substance was dissolved in chloroform, followed by the dropwise addition of 50 mg of butyl isocyanate. The obtained mixture was heated under reflux for 2 hours to conduct a reaction. After the completion of the reaction, the obtained reaction mixture was concentrated to precipitate a crystal. This crystal was recrystallized from an ethyl acetate/hexane mixture to give 190 mg of the title compound.

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 mixture was distilled
  6. customto remove the solvent
  7. extractionThe residue was extracted with 2N NaOH
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with a saturated aqueous solution of common salt
  10. dry with materialdried over magnesium sulfate
  11. distillationdistilled
  12. customto remove the solvent
  13. additiona mixture of cis- and trans-isomers
  14. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-c388c82fb09f4d449d8620bc593e815d
Source dataset
uspto-grants-1997_09
Patent number
US05668136

Reaction notes

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