4-Aminothiophenol → 4-(pyridin-3-ylmethylsulfanyl)aniline

HRID 856676Notes

Reaction equation

HRID 856676 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl.Cl[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1>CO>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][S:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 36420654-(pyridin-3-ylmethylsulfanyl)anilineYield 75.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-aminothiophenol (10 g) was dissolved in methanol (200 ml), aqueous solution of sodium hydroxide (15.7 g, 60 ml) was added to the mixture, 3-(chloromethyl)pyridine hydrochloride (14.4 g) was added to the mixture at 0° C., and the mixture was stirred for 2 hours at room temperature. The solvent was removed under reduced pressure, and the obtained residue was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 4-[(3-pyridinylmethyl)sulfanyl]aniline (13.1 g).

Workup

  1. additionwas added to the mixture at 0° C.
  2. customThe solvent was removed under reduced pressure
  3. additionthe obtained residue was added to water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-51bca4281f294e94a8dc810e41dd71aa
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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