Sodium Chloride → 1-(Ethylsulfanyl)-4-nitrobenzene

HRID 1027855Notes

Reaction equation

HRID 1027855 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[CH2:13](I)[CH3:14].[Cl-].[Na+]>C(O)C.O>[CH2:13]([S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:14]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 158094-Nitrobenzenethiol

Product 1

HCID 123213391-(Ethylsulfanyl)-4-nitrobenzeneYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

16.56 g (106.72 mmol) of 4-nitrothiophenol was added, while cooling with water, to a solution of 4.27 g (106.76 mmol) sodium hydroxide in 320 ml ethanol and it was stirred for 15 minutes at room temperature. Then, while cooling with water, 8.63 ml (106.79 mmol) of ethyl iodide was added and the mixture was stirred overnight at room temperature. The mixture was added to saturated sodium chloride solution and was extracted with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. Then it was dissolved in DCM and filtered again and evaporated to dryness. 16.86 g (92.02 mmol) of the raw product was obtained.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionwas extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. dissolutionThen it was dissolved in DCM
  8. filtrationfiltered again
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-298dec004d194a428acb527faaae0ef4
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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