Benzyl mercaptan → 2-(Benzylthio)-4-methylpyridine

HRID 880843

Reaction equation

HRID 880843 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[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1>O1CCCC1.O>[CH2:9]([S:10][C:12]1[CH:17]=[C:16]([CH3:18])[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 27340872-Bromo-4-methylpyridine

Product 1

HCID 583498362-(Benzylthio)-4-methylpyridineYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium hydride (60% in oil, 512 mg) in tetrahydrofuran (45 mL) was added dropwise phenylmethanethiol (1.52 g) at room temperature, 2-bromo-4-methylpyridine (2.0 g) was added, and the mixture was stirred at 60° C. for 72 hr. The reaction mixture was diluted with water and 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=24:1) to give the title compound as a brown oil (yield 1.40 g, 56%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washCombined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane→hexane-ethyl acetate=24:1)

Sources & evidence

ORD record
ord-29915f5cf86c43e8aa7d0ecb5d64947f
Source dataset
uspto-grants-2015_03
Patent number
US08993598B2

Linked notes

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