Sodium Hydroxide → 3-Chloro-4-[(3-pyridinylmethyl)sulfanyl]aniline

HRID 856702Notes

Reaction equation

HRID 856702 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([Cl:9])[CH:3]=1.[OH-].[Na+].Cl.Cl[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>CO>[Cl:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[NH2:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 135193524-Amino-2-chlorobenzenethiol

Product 1

HCID 136884333-Chloro-4-[(3-pyridinylmethyl)sulfanyl]anilineYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-amino-2-chlorobenzenethiol (1.2 g) was dissolved in methanol (24 ml), and to this solution was added 3N aqueous solution of sodium hydroxide (7.5 ml) and then, 3-(chloromethyl)pyridine hydrochloride (1.48 g), and the mixture was stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was 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 purified by silica gel column chromatography, to give 3-chloro-4-[(3-pyridinylmethyl)sulfanyl]aniline (0.83 g).

Workup

  1. customThe solvent was removed under reduced pressure, and water
  2. additionwas added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40958dffa4844222be177b3f8a38c61e
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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