Dimethyl Sulfoxide → 3-Chloro-5-ethoxypyridine

HRID 1266971Notes

Reaction equation

HRID 1266971 reaction equation
[Na].[CH2:2]([OH:4])[CH3:3].Cl[C:6]1[CH:7]=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1.CS(C)=O>O>[Cl:12][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([O:4][CH2:2][CH3:3])[CH:11]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 171533,5-DichloropyridineHCID 5360545Sodium

Product 1

HCID 115211283-Chloro-5-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sodium (8.1 g, 338 mmol) was added to ethanol (200 ml). After complete reaction, the excess of ethanol was evaporated. 3,5-Dichloropyridine (40.0 g, 270 mmol) and dimethyl sulfoxide (300 ml) were added to the crude mixture. The mixture was stirred at 70° C. for 1 h. Water (500 ml) was added, followed by extraction twice with ethyl acetate (300 ml). The product was isolated in quantitative yield.

Workup

  1. customAfter complete reaction
  2. customthe excess of ethanol was evaporated
  3. extractionfollowed by extraction twice with ethyl acetate (300 ml)
  4. customThe product was isolated in quantitative yield

Sources & evidence

ORD record
ord-ba53020053b546f6865c6fa290e6b107
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

Loading…