2,6-Dichloro-4-nitropyridine → 2,6-Dichloro-4-(methylthio)pyridine

HRID 1492365Notes

Reaction equation

HRID 1492365 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][S-:13].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([S:13][CH3:12])[CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

4

Reactant 2

HCID 38410702,6-Dichloro-4-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 189502312,6-Dichloro-4-(methylthio)pyridineYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichloro-4-nitropyridine (3.8 g; 0.02 mol) in dimethylformamide (50 ml) cooled with an ice-bath was sodium thiomethoxide (1.4 g; 0.02 mol) slowly added. After stirring for 3 hours, the reaction mixture was quenched with water (300 ml) and extracted 3 times each with a hexane/ethyl acetate mixture (100 ml; 1/1). The combined extracts were dried with anhydrous magnesium sulphate and the solvent was removed in vacuo. Purification by silica gel flash column chromatography afforded 2,6-dichloro-4-methylthiopyridine (2.9 g; 74%) as a colorless oil.

Workup

  1. additionslowly added
  2. customthe reaction mixture was quenched with water (300 ml)
  3. extractionextracted 3 times each with a hexane/ethyl acetate mixture (100 ml; 1/1)
  4. dry with materialThe combined extracts were dried with anhydrous magnesium sulphate
  5. customthe solvent was removed in vacuo
  6. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-7eadde4d1ac241ffbff21fb1c8f76752
Source dataset
uspto-grants-1994_12
Patent number
US05374604

Reaction notes

Loading…