Thiophenol → p-Toluenesulfonic acid

HRID 981340Notes

Reaction equation

HRID 981340 reaction equation
C1(S)C=CC=CC=1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.NC(C#N)C#N.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:8]1([CH3:18])[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10340Sodium CarbonateHCID 563049Aminomalononitrile p-toluenesulphonate

Product 1

HCID 6101p-Toluenesulfonic acidYield 147.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of thiophenol (10.5 g) and 2-aminomalononitrile p-toluenesulfonate (20 g) in acetonitrile (400 ml) was added sodium carbonate (21 g) at room temperature. After stirring for 10 hours, the solid residue was filtered and a half volume of the filtrate was evaporated under reduced. pressure to give the residue to which p-toluenesulfonic acid (20 g) was added. A precipitate solid formed was collected by filtration and thoroughly washed successively with acetonitrile and n-hexane to give 15 g of white crystales. Infrared sectrum of this compound was identical with that of 2,3-diamino-(3-phenylthio)acrylonitrile p-toluenesulfonate prepared in example 1.

Workup

  1. filtrationthe solid residue was filtered
  2. customa half volume of the filtrate was evaporated

Sources & evidence

ORD record
ord-43d60dc02a0b4d0083eefd2d2f0ec152
Source dataset
uspto-grants-1991_02
Patent number
US04990630

Reaction notes

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