Thiophenol → HCID 66727184, compound

HRID 1845948Notes

Reaction equation

HRID 1845948 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]=[CH:13][CH2:12][N:11](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[C@H:10]([CH3:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]=[CH:13][CH2:12][NH:11][C@H:10]([CH3:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 66727231HCID 66727231, compound

Product 1

HCID 66727184HCID 66727184, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

60 mg of the compound obtained in Step 4 was dissolved in 5 mL of acetonitrile, and 100 mg of potassium carbonate and 0.03 mL of thiophenol were added thereto with stirring at room temperature. After stirring at room temperature for 6 hours, the reaction solution was diluted with water, followed by extraction with dichloromethane (50 mL×2). Then, the extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (methanol:dichloromethane=1:10) to obtain 25 mg of the compound of interest as a colorless oil (76%).

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. extractionfollowed by extraction with dichloromethane (50 mL×2)
  3. dry with materialThen, the extract was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (methanol:dichloromethane=1:10)

Sources & evidence

ORD record
ord-f2c7281456b94dfb8f40013fe974725a
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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