p-Toluenesulfonic acid → HCID 15672405, compound

HRID 2255208Notes

Reaction equation

HRID 2255208 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1)=O.[CH:17]([SH:20])(S)[CH3:18].C1(C)C=CC([S:27](O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[S:20]1[CH2:17][CH2:18][S:27][CH:1]1[C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 336451,1-EthanedithiolHCID 15672397HCID 15672397, compound

Product 1

HCID 15672405HCID 15672405, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of dimethyl 5-formylpyridine-2,3-dicarboxylate (0.73 g, 0.00327 mol), ethanedithiol (0.357 mL, 0.00425 mol) and a catalytic amount of para-toluenesulfonic acid in chloroform (20 mL) is heated at reflux for 5.5 hours. During this time, water is removed by placement of an addition funnel containing 3 angstrom molecular sieves in between the reaction flask and the reflux condensor. After cooling, the reaction is diluted with methylene chloride (20 mL) and is washed with 10% aqueous sodium carbonate and saturated sodium chloride solutions. The organic solution is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue. The residue is purified by chromatography using silica gel and 33% ethyl acetate in hexanes as eluant to yield the title compound as a clear oil (0.66 g, 67%), identified by IR and NMR spectral analyses.

Workup

  1. temperatureat reflux for 5.5 hours
  2. customDuring this time, water is removed by placement of an addition funnel
  3. additioncontaining 3 angstrom molecular sieves in between the reaction flask
  4. temperatureAfter cooling
  5. additionthe reaction is diluted with methylene chloride (20 mL)
  6. washis washed with 10% aqueous sodium carbonate and saturated sodium chloride solutions
  7. dry with materialThe organic solution is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-4e1e0babb0a245f591d063563c21fbb4
Source dataset
uspto-grants-1993_08
Patent number
US05239070

Reaction notes

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