1,2-Ethanedithiol → 2-[2-(1-Imidazolyl)ethylthio]ethanethiol

HRID 1654166Notes

Reaction equation

HRID 1654166 reaction equation
[CH2:1]([SH:4])[CH2:2][SH:3].C[O-].[Na+].Cl[CH2:9][CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1>C(O)C>[N:11]1([CH2:10][CH2:9][S:3][CH2:2][CH2:1][SH:4])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 27575041-(2-Chloroethyl)imidazoleHCID 10942334Sodium Methoxide

Product 1

HCID 541040582-[2-(1-Imidazolyl)ethylthio]ethanethiol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (30 ml) was dissolved 1-(2-chloroethyl)imidazole, to which were added 1,2-ethanedithiol (25 ml) and sodium methoxide (28% methanol solution) (16.6 ml), and the mixture was heated for 30 minutes under reflux. Insoluble substances were filtered off, and the filtrate was concentrated under reduced pressure. To the concentrate was added dichloromethane (300 ml). The organic layer was washed with water, then with a saturated aqueous sodium chloride solution, followed by drying (sodium sulfate). The solvent was distilled off, and the residue was subjected to a silica gel column chromatography (3.0×40 cm:ethyl acetate→ethyl acetate:methanol=10:1) to give 2-[2-(1 -imidazolyl)ethylthio]ethanethiol (3.0 g) as a pale yellow oily substance.

Workup

  1. temperaturethe mixture was heated for 30 minutes
  2. temperatureunder reflux
  3. filtrationInsoluble substances were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the concentrate was added dichloromethane (300 ml)
  6. washThe organic layer was washed with water
  7. dry with materialby drying (sodium sulfate)
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2605257a3ceb4b61b602a46f4f99ec98
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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