Thiophenol → HCID 67544690, compound

HRID 2061013Notes

Reaction equation

HRID 2061013 reaction equation
[C:1]1([NH:7][C:8]([C:10]#[C:11][CH3:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[C:1]1([N:7]=[C:8]([S:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[C:11]([S:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 24819Phosphorus pentachlorideHCID 1285856156776-81-9

Product 1

HCID 67544690HCID 67544690, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.76 g (4.8 mmol) of N-phenyl-1-propynecarboxamide in toluene (15 mL) was added 1.0 g (4.8 mmol) of phosphorus pentachloride at room temperature and stirred for 4 hours. After removal of the solvent, the residue was dissolved in DMF (15 mL). To a solution of 1.2 mL (12 mmol) of thiophenol in DMF (15 mL) was added 0.31 g (7.1 mmol) of sodium hydride (60% in oil) under ice cooling and stirred for 0.5 hours. The mixture was added to the above-described DMF solution of the residue and stirred under ice cooling for 3 hours. After dilution with tert-butyl methyl ether (150 mL), the mixture was washed sequentially with water and a saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 0.39 g of phenyl N-phenyl-3-(phenylthio)-2-butenimidothioate (hereinafter referred to as the present compound 44).

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in DMF (15 mL)
  3. stirringstirred for 0.5 hours
  4. stirringstirred under ice cooling for 3 hours
  5. washAfter dilution with tert-butyl methyl ether (150 mL), the mixture was washed sequentially with water
  6. dry with materiala saturated NaCl solution, dried over anhydrous MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-72c962fc88a746ca9988fb076c35dc7e
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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