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

HRID 2259740Notes

Reaction equation

HRID 2259740 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. 312 g of thiourea was added to the solution and the mixture was heated under reflux on a boiling water bath for 2 h. The reaction mixture was cooled. A solution of 300 g of sodium hydroxide in 1 l of water was added thereto and the mixture was heated under reflux on a boiling water bath for 45 min. After cooling, 3 l of water was added thereto and the product was extracted with 5 l of ethyl acetate. The extract was washed with dilute hydrochloric acid. It was then washed with water until the washing became substantially neutral and dried over anhydrous sodium sulfate. The solvent was distilled off at 40° C. to obtain about 570 g of a faint yellow oil. It was purified according to column chromatography with about 3 kg of silica gel (hexane:benzene=2:1) to obtain 310 g of the intended compound in the form of a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux on a boiling water bath for 2 h
  3. temperatureThe reaction mixture was cooled
  4. temperaturethe mixture was heated
  5. temperatureunder reflux on a boiling water bath for 45 min
  6. temperatureAfter cooling
  7. extractionthe product was extracted with 5 l of ethyl acetate
  8. washThe extract was washed with dilute hydrochloric acid
  9. washIt was then washed with water until the washing
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off at 40° C.

Sources & evidence

ORD record
ord-c9cc653e629249ab8b596feaf0b4ef84
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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