Thiophenol → HCID 53415250, compound

HRID 1893495Notes

Reaction equation

HRID 1893495 reaction equation
[CH:1]([N:4]([CH2:12][CH2:13][NH:14]S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C(#N)C.O>[NH2:14][CH2:13][CH2:12][N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66880067HCID 66880067, compound

Product 1

HCID 53415250HCID 53415250, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The compound (34.21 g, 82.60 mmol) obtained in step A was dissolved in acetonitrile (300 ml), cesium carbonate (52.38 g, 161 mmol) and benzenethiol (12 ml, 117 mmol) were added and the mixture was stirred at room temperature for one day. The reaction mixture was diluted with water, and the aqueous layer was extracted with dichloromethane. The obtained organic layer was dried over potassium carbonate, the insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was dissolved in toluene, and the mixture was extracted with 1N aqueous hydrogensulfate potassium solution. An aqueous sodium hydroxide solution was added to the aqueous layer to give a strong alkaline solution, and the suspending oil was extracted. The aqueous layer was extracted with dichloromethane, mixed with oil and dichloromethane solution, and the mixture was dried over sodium sulfate. The insoluble material was filtered off and the solution was concentrated under reduced pressure to give the title compound as a pale-yellow oil (15.0 g, yield 79%).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe obtained organic layer was dried over potassium carbonate
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe solution was concentrated under reduced pressure
  5. dissolutionThe obtained oil was dissolved in toluene
  6. extractionthe mixture was extracted with 1N aqueous hydrogensulfate potassium solution
  7. additionAn aqueous sodium hydroxide solution was added to the aqueous layer
  8. customto give a strong alkaline solution
  9. extractionthe suspending oil was extracted
  10. extractionThe aqueous layer was extracted with dichloromethane
  11. additionmixed with oil and dichloromethane solution
  12. dry with materialthe mixture was dried over sodium sulfate
  13. filtrationThe insoluble material was filtered off
  14. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7e820167a2e46869d5cc85229783fc1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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