Benzyl mercaptan → 3-Methyl-2-(phenylmethylthio)-pyridine

HRID 880841Notes

Reaction equation

HRID 880841 reaction equation
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1>O1CCCC1.O>[CH2:9]([S:10][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 2208322-Bromo-3-methylpyridine

Product 1

HCID 146531873-Methyl-2-(phenylmethylthio)-pyridineYield 222.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 1.44 g) in tetrahydrofuran (45 mL) was added dropwise phenylmethanethiol (465 mg) at room temperature and the mixture was stirred for 15 min. 2-Bromo-3-methylpyridine (2.0 g) was added to the reaction mixture, and the mixture was stirred at 60° C. for 1.5 hr. The reaction mixture was diluted with water, and concentrated under reduced pressure. The residual aqueous layer was extracted twice with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane→hexane-ethyl acetate=97:3) to give the title compound as a gray oil (yield 1.79 g, 72%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 1.5 hr
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residual aqueous layer was extracted twice with ethyl acetate
  4. washCombined organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:hexane→hexane-ethyl acetate=97:3)

Sources & evidence

ORD record
ord-9b4955dcc2884fe1b4816d057161f919
Source dataset
uspto-grants-2015_03
Patent number
US08993598B2

Reaction notes

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