Sodium methanethiolate → 2-[[2-(Methylthio)-3-pyridinyl]oxy]ethanol

HRID 493344Notes

Reaction equation

HRID 493344 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:10]([O:11][CH2:12][CH2:13][OH:14])=[CH:9][CH:8]=[CH:7][N:6]=1>CN(C=O)C>[CH3:1][S:2][C:5]1[C:10]([O:11][CH2:12][CH2:13][OH:14])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 22036312HCID 22036312, compound

Product 1

HCID 220363602-[[2-(Methylthio)-3-pyridinyl]oxy]ethanolYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium thiomethoxide (3.01 g, 42.9 mmol) in dry DMF (30 mL) was 2-[(2-chloro-3-pyridinyl)oxy]ethanol (7.82 g, 45.1 mmol, from Example 193, Step 1) added and the reaction mixture was stirred at ambient temperature for 1 h.. The solvent was removed under reduced pressure and the residue was partitioned between brine/1 M aqueous NaOH and CHCl3. The aqueous phase was extracted with an additional portion of CHCl3 and the combined organic layers were dried (MgSO4) and concentrated. The resulting red oil was purified by column chromatography on silica using toluene/Et3N/MeOH (96:2:2) as eluent to give 3.0 g (36%) of the title compound as brownish crystals: mp 80° C. Anal. (C7H11NO2S) C, H, N.

Workup

  1. additionadded
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between brine/1 M aqueous NaOH and CHCl3
  4. extractionThe aqueous phase was extracted with an additional portion of CHCl3
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe resulting red oil was purified by column chromatography on silica

Sources & evidence

ORD record
ord-2850c802cfc54543aaf782c2b8f5a2cf
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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