Sodium Hydroxide → 2-(1,3-Benzodioxol-5-yl)ethanethiol

HRID 486927Notes

Reaction equation

HRID 486927 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1.NC(N)=[S:15].[OH-].[Na+]>C(O)C.O>[O:8]1[C:7]2[CH:11]=[CH:12][C:4]([CH2:3][CH2:2][SH:15])=[CH:5][C:6]=2[O:10][CH2:9]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 122072243,4-Methylenedioxyphenethyl bromide

Product 1

HCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiolYield 95.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

750 g of 5-(2-bromoethyl)-1,3-benzodioxole was dissolved in 1 l of ethanol, followed by the addition of 312 g of thiourea. The mixture was heated under reflux on a boiling water bath for 2 hours and cooled, followed by the addition of a solution of 300 g of sodium hydroxide in 1 l of water. The obtained mixture was heated under reflux on a boiling water bath for 45 minutes and cooled, followed by the addition of 3 l of water. The obtained mixture was extracted with 5 l of ethyl acetate. The extract was washed with dilute hydrochloric acid and with water until the washings became neutral, dried over anhydrous sodium sulfate and distilled at 40° C. to remove the solvent. About 570 g of a yellow oil was obtained. This oil was purified by silica gel column chromatography (hexane/benzene=2:1) to obtain 310 g of the title compound as a colorless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux on a boiling water bath for 2 hours
  3. temperaturecooled
  4. temperatureThe obtained mixture was heated
  5. temperatureunder reflux on a boiling water bath for 45 minutes
  6. temperaturecooled
  7. extractionThe obtained mixture was extracted with 5 l of ethyl acetate
  8. washThe extract was washed with dilute hydrochloric acid and with water until the washings
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationdistilled at 40° C.
  11. customto remove the solvent

Sources & evidence

ORD record
ord-86008ed6779e4fb4bf5387d5b0ef6286
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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