Sodium Hydroxide → 2-[[(2-Methyl-4-nitrophenyl)sulfanyl]methyl]pyridine

HRID 856681Notes

Reaction equation

HRID 856681 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[SH:11].[OH-].[Na+].Cl.Cl[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 107734502-Methyl-4-nitrobenzenethiol

Product 1

HCID 695222562-[[(2-Methyl-4-nitrophenyl)sulfanyl]methyl]pyridineYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-4-nitrobenzenethiol (3.0 g) was dissolved in THF (60 ml), and to this solution was added aqueous solution of sodium hydroxide (2.1 g, 15 ml) and then, 2-(chloromethyl)pyridine hydrochloride (3.5 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 washed with hexane/ethyl acetate, to give 2-[[(2-methyl-4-nitrophenyl)sulfanyl]methyl]pyridine (3.4 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. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-aa6b8c9255bc4b16974f3caeded54c18
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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