4-Methylbenzenethiol → HCID 88076664, compound

HRID 397603

Reaction equation

HRID 397603 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1SCl)([O-:11])=[O:10]>C(#N)C.[Ag]>[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[C:7]1[CH:6]=[C:5]([S:8][S:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([C:13]3[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=3[N+:9]([O-:11])=[O:10])[CH:6]=2)[CH:4]=[CH:3][C:2]=1[CH3:1])([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 78114-MethylbenzenethiolHCID 682512,4-Dinitrobenzenesulfenyl chloride

Product 1

HCID 88076664HCID 88076664, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 6342AcetonitrileSolvent

Procedure

In a nitrogen atmosphere, 3.70 g (16.0 mmol) of the silver salt of p-thiocresol and 3.75 g (16.0 mmol) of 2,4-dinitrophenylsulfenyl chloride were stirred for 3 hours in 150 ml of acetonitrile serving as a solvent, while cooling with ice water. The reaction mixture was filtered and the residue obtained after the concentration of the filtrate under reduced pressure was subjected to chromatography on a silica gel column (eluting solvent: hexane/ethyl acetate=5/1), whereby 1.64 g (5.08 mmol, yield: 31.8%) of 2,4-dinitrophenyl p-tolyldisulfide were obtained as yellow crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe residue obtained after the concentration of the filtrate under reduced pressure
  3. washwas subjected to chromatography on a silica gel column (eluting solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-6754866044f34132be81ff2175324272
Source dataset
uspto-grants-2003_08
Patent number
US06610708B1

Linked notes

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