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

HRID 856697Notes

Reaction equation

HRID 856697 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[OH-].[Na+].Cl.Cl[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>CO>[CH3:10][O:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[NH2:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 193920294-Amino-2-methoxybenzene-1-thiol

Product 1

HCID 695220573-Methoxy-4-[(3-pyridinylmethyl)sulfanyl]anilineYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-amino-2-methoxybenzenethiol (1.0 g) was dissolved in methanol (20 ml), and to this solution was added 3N aqueous solution of sodium hydroxide (6.4 ml) and then, 3-(chloromethyl)pyridine hydrochloride (1.27 g), and the mixture was stirred for 30 minutes. The solvent was removed under reduced pressure, and the residue 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-methoxy-4-[(3-pyridinylmethyl)sulfanyl]aniline (1.0 g).

Workup

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

Sources & evidence

ORD record
ord-4c75146ccd1148ff808f099b1fc5caa6
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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