Water → Bis-[2-(3-methylindole-1-yl)ethyl]disulfide

HRID 1657746Notes

Reaction equation

HRID 1657746 reaction equation
[S:1]([O-])([O-])(=O)=[S:2].[Na+].[Na+].O.Br[CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH3:21])=[CH:13]1>C(O)C>[CH3:21][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([CH2:11][CH2:10][S:1][S:2][CH2:10][CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH3:21])=[CH:13]2)[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 213895541-(2-Bromoethyl)-3-methylindole

Product 1

HCID 21389563Bis-[2-(3-methylindole-1-yl)ethyl]disulfide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.4 g. of sodium thiosulfate in 60 ml. of water and 100 ml. of ethanol is poured onto 8.6 g. of 1-(2-bromoethyl)-3-methylindole. The reactionmixture is stirred and heated at reflux for 3.5 hr., allowed to cool, and evaporated to dryness. The solid residue is dissolved in boiling isopropanol, dried with a hydrated alkali-aluminum silicate ("Molecular Sieves"), and filtered. Chilling of the filtrate causes 6.4 g. of the sodium indolyethyl thiosulfate derivative to precipitate. This material is collected by filtration and washed with ether. The isolated intermediate is heated at reflux with a solution of sodium hydroxide (9 g. of NaOH, 60 ml. of water, 140 ml. of ethanol) for 3 hr. Ethanol is removed under reduced pressure, the aqueous residue diluted with water and extracted with three portions of ether. Combined ether extracts are washed with water, saturated brine solution, and dried over magnesium sulfate. The filtrate is evaporated, to yield bis-[2-(3-methylindole-1-yl)ethyl]disulfide.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 hr
  3. temperatureto cool
  4. customevaporated to dryness
  5. dissolutionThe solid residue is dissolved
  6. dry with materialdried with a hydrated alkali-aluminum silicate ("Molecular Sieves")
  7. filtrationfiltered
  8. temperatureChilling of the filtrate causes 6.4 g
  9. customof the sodium indolyethyl thiosulfate derivative to precipitate
  10. filtrationThis material is collected by filtration
  11. washwashed with ether
  12. temperatureThe isolated intermediate is heated
  13. temperatureat reflux with a solution of sodium hydroxide (9 g. of NaOH, 60 ml. of water, 140 ml. of ethanol) for 3 hr
  14. customEthanol is removed under reduced pressure
  15. additionthe aqueous residue diluted with water
  16. extractionextracted with three portions of ether
  17. washCombined ether extracts are washed with water, saturated brine solution
  18. dry with materialdried over magnesium sulfate
  19. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-4ba59820066b48328aa98abb1b556bb2
Source dataset
uspto-grants-1976_06
Patent number
US03962236

Reaction notes

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