Sodium hydride → HCID 22624973, compound

HRID 279625Notes

Reaction equation

HRID 279625 reaction equation
[H-].[Na+].[SH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.Br[CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1>CN(C=O)C.O>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][CH2:12][CH2:11][S:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 178418431pyridine-4-thiol

Product 1

HCID 22624973HCID 22624973, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydride (890 mg of a 50% suspension in mineral oil, 19 mmol) was added to a solution of 4-mercaptopyridine (2.34 g, 21 mmol) in DMF (75 ml) and the mixture stirred for 30 minutes. 2-(2-Bromoethoxy)tetrahydropyran (4.0 g, 19 mmol), (J. Am. Chem. Soc. 1948, 70, 4187), was added and the mixture heated at 100° C. for 3 hours and then stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3) to give 4-(2-(tetrahydropyran-2-yloxy)ethylthio)pyridine (2.8 g, 56%).

Workup

  1. stirringstirred at ambient temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3)

Sources & evidence

ORD record
ord-782740c22c6b491488cec5af9748443f
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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