Sodium Hydroxide → 2-(1,3-Benzodioxol-5-yl)ethyl (pyridin-4-yl)methyl sulfide

HRID 2259761Notes

Reaction equation

HRID 2259761 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.[OH-].[Na+].Cl.[N:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1>C(O)C>[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][S:12][CH2:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiol

Product 1

HCID 158195132-(1,3-Benzodioxol-5-yl)ethyl (pyridin-4-yl)methyl sulfideYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

3.30 g of 2-(1,3-benzodioxol-5-yl)ethanethiol was dissolved in 30 ml of ethanol. 1.65 g of sodium hydroxide and then 2.70 g of 4-picolyl chloride hydrochloride were added to the solution and the mixture was heated under reflux at 70° C. for 30 min. The solvent was distilled off and water was added to the residue. After extraction with ethyl acetate, 1N hydrochloric acid was added to the extract. The aqueous layer was acidified, taken up and washed with ethylacetate. The pH of the aqueous layer was adjusted to 8 with potassium carbonate. After extraction with ethyl acetate, the extract was washed with a saturated aqueous common salt solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off and the residue was purified according to silica gel column chromatography (ethyl acetate/hexane=1:4) to obtain 2.69 g of the intended compound in the form of a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. distillationThe solvent was distilled off
  3. additionwater was added to the residue
  4. extractionAfter extraction with ethyl acetate, 1N hydrochloric acid
  5. additionwas added to the extract
  6. washwashed with ethylacetate
  7. extractionAfter extraction with ethyl acetate
  8. washthe extract was washed with a saturated aqueous common salt solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration
  11. distillationthe solvent was distilled off
  12. customthe residue was purified

Sources & evidence

ORD record
ord-7d7af1deb008489dacc8b48b856500fb
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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