3-Phenylprop-2-Enal → 5-(4-Phenyl-1,3-butadienyl)-1,2-dithiol-3-thione

HRID 845739Notes

Reaction equation

HRID 845739 reaction equation
[Mg].[CH:2](=O)[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:12][C:13]1[S:17][S:16][C:15](=[S:18])[CH:14]=1>CO>[C:5]1([CH:4]=[CH:3][CH:2]=[CH:12][C:13]2[S:17][S:16][C:15](=[S:18])[CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 1378993H-1,2-Dithiole-3-thione, 5-methyl-HCID 5462224Magnesium2×

Product 1

HCID 539425735-(4-Phenyl-1,3-butadienyl)-1,2-dithiol-3-thione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 40 ml of methanol, 600 mg (24 milligrams atom) of magnesium metal was added, and the mixture was heated to reflux for 1 hour to dissolve the magnesium metal. While cooling the mixture in ice water, 1.4 g (10 milli moles) of cinnamaldehyde, and then 1.56 g (10 milli moles) of 5-methyl-1,2-dithiol-3-thione were added to the mixture and the mixture was stirred for 1 hour at the same temperature. Separated crystals were recovered by filtration, and were added to 300 ml of ethyl acetate. Insolubles were removed by filtration, and the mother liquor was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude crystals were recrystallized from benzene-ethanol to obtain dark red crystals of

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customSeparated crystals
  4. filtrationwere recovered by filtration
  5. additionwere added to 300 ml of ethyl acetate
  6. customInsolubles were removed by filtration
  7. washthe mother liquor was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained crude crystals
  11. customwere recrystallized from benzene-ethanol
  12. customto obtain dark red crystals of

Sources & evidence

ORD record
ord-cd802792d5ad44bd8cd398c1329754d6
Source dataset
uspto-grants-1988_07
Patent number
US04760078

Reaction notes

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