Thiophenol → Benzene, 1,4-bis(phenylthio)-

HRID 1758464Notes

Reaction equation

HRID 1758464 reaction equation
[OH-].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC(N(C)C)=O>[S:9]([C:6]1[CH:7]=[CH:8][C:3]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:4][CH:5]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 14797Potassium Hydroxide

Product 1

HCID 626321Benzene, 1,4-bis(phenylthio)-Yield 45%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 19.6 parts of 86% potassium hydroxide, 33 parts of thiophenol and about 120 parts of dimethylacetamide was heated at a temperature of 120° C. with stirring to effect the removal of water. After about 6.5 parts of water was collected, there was added to the resulting mixture 26.3 parts of para-dibromobenzene and the mixture was heated to reflux. After 6 hours at reflux the reaction mixture was allowed to cool and 300 parts of water was added. There was obtained a tan colored solid which was filtered and washed with water several times. The product was then dried. There was obtained 34.7 parts of 1,4-dithiophenoxybenzene based on method of preparation.

Workup

  1. customthe removal of water
  2. customAfter about 6.5 parts of water was collected
  3. additionthere was added to the resulting mixture 26.3 parts of para-dibromobenzene
  4. temperaturethe mixture was heated to reflux
  5. temperatureAfter 6 hours at reflux the reaction mixture
  6. temperatureto cool
  7. addition300 parts of water was added
  8. customThere was obtained a tan colored solid which
  9. filtrationwas filtered
  10. washwashed with water several times
  11. customThe product was then dried

Sources & evidence

ORD record
ord-d72ff935581a4e1491155cb8924c2301
Source dataset
uspto-grants-1983_02
Patent number
US04374066

Reaction notes

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