Dimethyl Disulfide → HCID 22678645, compound

HRID 1837711Notes

Reaction equation

HRID 1837711 reaction equation
C([Li])CCC.[CH3:6][O:7][CH:8]([O:18][CH3:19])[C:9]1[C:10]([O:16][CH3:17])=[N:11][CH:12]=[C:13](Br)[CH:14]=1.[CH3:20]SSC.C(=O)(O)[O-].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[S:40]([O-:44])([O-])(=[O:42])=S.[Na+].[Na+]>O1CCCC1.ClCCl.O>[CH3:6][O:7][CH:8]([O:18][CH3:19])[C:9]1[C:10]([O:16][CH3:17])=[N:11][CH:12]=[C:13]([S:40]([CH3:20])(=[O:44])=[O:42])[CH:14]=1

Participants

10

Reactant 6

HCID 12232Dimethyl DisulfideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22678608HCID 22678608, compoundHCID 178418339Butyllithium

Product 1

HCID 22678645HCID 22678645, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

20 ml of tetrahydrofuran was cooled to −78° C., 4.17 ml of n-butyllithium (1.6 M, hexane solution) was added thereto, and the mixture was stirred. A solution of 1.59 g of 5-bromo-2-methoxy-3-pyridinecarboxaldehyde dimethyl acetal dissolved in 5 ml of tetrahydrofuran was added dropwise thereinto. After 30 minutes, 0.66 ml of dimethyldisulfide was added dropwise thereinto, and the mixture was further stirred for 1.5 hours. water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a pale yellow oil. The oil was dissolved in 30 ml of dichloromethane, 5.12 g of sodium bicarbonate and 2.32 g of m-chloroperbenzoic acid were added thereto, and the mixture was stirred for 30 minutes under ice-cooling. An aqueous sodium thiosulfate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, a 1N aqueous sodium hydroxide and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to give 0.81 g of the title compound as a white solid.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was further stirred for 1.5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a pale yellow oil
  8. stirringthe mixture was stirred for 30 minutes under ice-
  9. temperaturecooling
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with water
  12. dry with materiala 1N aqueous sodium hydroxide and brine, and then dried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customthe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-857207e52b6446f8af4c6d3cdc0d922b
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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