Water → HCID 60735499, compound

HRID 1672401Notes

Reaction equation

HRID 1672401 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[C:9]([O-])([O-])=O.[K+].[K+].C[CH:16]([SH:20])[C:17]([O-:19])=[O:18].O>CN(C=O)C>[CH3:9][O:19][C:17](=[O:18])[CH2:16][S:20][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 276852,5-DichloropyridineHCID 156077362-Mercaptopropionate

Product 1

HCID 60735499HCID 60735499, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-dichloropyridine (13, 2.04 g, 13.8 mmol) in 40 mL of dry DMF was added K2CO3 (1.91 g, 13.8 mmol) and reaction mixture was stirred for 30 min at ambient temperature. Neat methylthioglycolate (1.26 mL, 14 mmol) was added via syringe and the reaction mixture was stirred overnight under N2. The reaction mixture was treated with H2O (120 mL) and the product was extracted into EtOAc (2×220 mL). Combined organic layers were washed with lot of water, brine, dried over Na2SO4, filtered and concentrated to give 2.3 g of crude material which was purified by column chromatography (hexanes/EtOAc). Obtained 1.1 g (5.0 mmol) of target 14, as a colorless oil, in 36% yield.

Workup

  1. stirringthe reaction mixture was stirred overnight under N2
  2. extractionthe product was extracted into EtOAc (2×220 mL)
  3. washCombined organic layers were washed with lot of water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-683ed55238ef441a89611373bc16e849
Source dataset
uspto-grants-2011_08
Patent number
US07998980B2

Reaction notes

Loading…