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

HRID 486923Notes

Reaction equation

HRID 486923 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 ethyl acetate. 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 ethyl acetate
  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-b0440f5b26f44876a61c083c44017ee0
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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