Chloroacetone → [{2-(1,3-Benzodioxol-5-yl)ethyl}thio]propan-2-one

HRID 486921Notes

Reaction equation

HRID 486921 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][SH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl[CH2:14][C:15](=[O:17])[CH3:16].[OH-].[Na+]>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:14][C:15](=[O:17])[CH3:16])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 14798Sodium HydroxideHCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiol

Product 1

HCID 22367134[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]propan-2-oneYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of 2-(1,3-benzodioxol-5-yl)ethanethiol and 5.1 g of 1-chloro-2-propanone were dissolved in 200 ml of 90% ethanol. 2.2 g of sodium hydroxide was added to the solution and the mixture was heated under reflux for 10 min to conduct the reaction. The reaction mixture was concentrated under reduced pressure. 200 ml of ethyl acetate was added thereto to obtain a solution, which was washed with water three times. After drying over anhydrous sodium sulfate, the solvent was distilled off and the residue was purified according to silica gel column chromatography (benzene/ethyl acetate=30:1) to obtain 11.1 g of the intended compound in the form of a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 min
  3. customthe reaction
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. addition200 ml of ethyl acetate was added
  6. customto obtain a solution, which
  7. washwas washed with water three times
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customthe residue was purified

Sources & evidence

ORD record
ord-e44b5e7e3aaa4b7a830ed121181249f4
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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