Sulfuric Acid → 2-(2-Tosylethylthio)nicotinic acid

HRID 660051Notes

Reaction equation

HRID 660051 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11]1([CH3:23])[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21]O)(=[O:19])=[O:18])=[CH:13][CH:12]=1.OS(O)(=O)=O>CN(C=O)C>[S:17]([CH2:20][CH2:21][S:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([C:14]1[CH:15]=[CH:16][C:11]([CH3:23])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 178524460HCID 178524460, compound

Product 1

HCID 687267972-(2-Tosylethylthio)nicotinic acidYield 14.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7.3 g (47 mmol) of 2-mercaptonicotinic acid and 9.6 g (48 mmol) of 2-(p-toluenesulfonyl)-ethanol was dissolved in DMF (80 ml). 0.5 ml of conc. H2SO4 was then carefully added dropwise, and stirring was carried out overnight under reflux. The reaction mixture was concentrated using a Genevac (EZ2). The residue was dissolved in acetonitrile and the solid was separated off. The mother liquor was concentrated, and MeOH was added. The resulting solid was filtered off and dried. 2.35 g (7 mmol, 14.8%) of 2-(2-tosylethylthio)nicotinic acid were obtained as solid.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in acetonitrile
  4. customthe solid was separated off
  5. concentrationThe mother liquor was concentrated
  6. additionMeOH was added
  7. filtrationThe resulting solid was filtered off
  8. customdried

Sources & evidence

ORD record
ord-11d018d06d50488199d2b9b4a624a474
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

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