p-Chlorothiophenol → HCID 14922885, compound

HRID 1253040Notes

Reaction equation

HRID 1253040 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 835721-Chloropinacolone

Product 1

HCID 14922885HCID 14922885, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 14.45 g quantity of p-chlorothiophenol and 13.8 g of anhydrous potassium carbonate were added to 200 ml of acetonitrile, and 13.45 of 1-chloro-3,3-dimethyl-2-butanone was added in small portions to the mixture while stirring the mixture. After stirring the mixture at 70° to 75° C. for 6 hours, the solid separating out was filtered off. The filtrate was concentrated to obtain a residue, which was subjected to extraction with benzene. To the extract was added 200 ml of 10% sodium hydroxide solution, followed by stirring at room temperature for 1 hour. The benzene layer was separated off, washed with water, then dried over anhydrous magnesium sulfate and distilled in a vacuum to remove the solvent, giving 20.2 g of the above-identified desired compound in the form of a pale yellow oil.

Workup

  1. additionwas added in small portions to the mixture
  2. stirringAfter stirring the mixture at 70° to 75° C. for 6 hours
  3. customthe solid separating out
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated
  6. customto obtain a residue, which
  7. extractionwas subjected to extraction with benzene
  8. additionTo the extract was added 200 ml of 10% sodium hydroxide solution
  9. stirringby stirring at room temperature for 1 hour
  10. customThe benzene layer was separated off
  11. washwashed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationdistilled in a vacuum
  14. customto remove the solvent

Sources & evidence

ORD record
ord-b4e7866124d2449da239185df50af5e2
Source dataset
uspto-grants-1988_05
Patent number
US04746673

Reaction notes

Loading…