Ethylene Glycol → HCID 86643578, compound

HRID 2201021Notes

Reaction equation

HRID 2201021 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)CO.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CC(O)C>[Cl:1][C:2]1[C:7]([S:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 242292082-Chloro-3-iodopyridin-4-amine

Product 1

HCID 86643578HCID 86643578, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

Into a 250 mL round bottom flask was placed the 2-chloro-3-iodo-4-aminopyridine (3.0 g, 11.8 mmol), thiophenol (1.3 g, 11.8 mmol), copper(I) iodide (0.11 g, 0.58 mmol), ethylene glycol (1.5 g, 24 mmol) and potassium carbonate (3.3 g, 24 mol). 100 mL of 2-propanol was then added to the reaction mixture and the mixture was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and was filtered under vacuum. The filtrate was diluted with 200 mL of water then was extracted two times with 150 mL of ethyl acetate. The extracts were dried over magnesium sulfate then were filtered and stripped under vacuum. The product was purified using Silica gel chromatography with 2-15% ethyl acetate/dichloromethane as the mobile phase. 2.0 g (72% yield of product was collected.

Workup

  1. customInto a 250 mL round bottom flask was placed
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 18 h
  4. filtrationwas filtered under vacuum
  5. additionThe filtrate was diluted with 200 mL of water
  6. extractionthen was extracted two times with 150 mL of ethyl acetate
  7. dry with materialThe extracts were dried over magnesium sulfate
  8. filtrationthen were filtered
  9. customThe product was purified

Sources & evidence

ORD record
ord-6025beff4e684ae3929c9ca2e7961392
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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