p-Chlorothiophenol → HCID 67213328, compound

HRID 1817170Notes

Reaction equation

HRID 1817170 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 67213328HCID 67213328, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (15 mL) were suspended ethyl 4-chloro-3-nitrobenzoate (1.10 g, 4.79 mmol), 4-chlorothiophenol (0.72 g, 4.98 mmol) and potassium carbonate (0.95 g, 6.78 mmol), and the suspension was heated under refluxing for 3 hours. The mixture was then placed under reduced pressure to distill the solvent off. After addition of water (100 mL), the mixture was subjected to extraction with ethyl acetate (100 mL×2) and dried over anhydrous sodium sulfate. The dry extract was placed under reduced pressure to distill the solvent off. The residue was purified-by silica gel column chromatography (ethyl acetate/hexane), to obtain 767 mg (yield 47%) of the titled compound as a yellow crystalline product.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder refluxing for 3 hours
  3. distillationto distill the solvent off
  4. additionAfter addition of water (100 mL)
  5. extractionthe mixture was subjected to extraction with ethyl acetate (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. extractionThe dry extract
  8. distillationto distill the solvent off

Sources & evidence

ORD record
ord-e1931649ab7741f78e589b85394af8a5
Source dataset
uspto-grants-2009_10
Patent number
US07598254B2

Reaction notes

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