Ethylene Glycol → HCID 86643578, compound

HRID 1848957Notes

Reaction equation

HRID 1848957 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.C(O)(C)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 91%

Reagents, catalysts & solvents 2

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

Procedure

To a 250 mL round flask was added 2-chloro-3-iodo-4-aminopyridine (5.0 g, 19.6 mmol), thiophenol (2.16 g, 19.6 mmol), CuI (0.187 g, 0.98 mmol), ethylene glycol (2.5 g, 39 mmol), potassium carbonate (5.4 g, 39 mmol), and 150 mL of isopropanol. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 24 h. After cooling, the mixture was purified by a silica gel column. Yield (91%) of 2-chloro-3-phenylthio-4-aminopyridine was 4.2 g.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe mixture was purified by a silica gel column

Sources & evidence

ORD record
ord-c72578119b7f424d89ee276df3a1e5cd
Source dataset
uspto-grants-2015_02
Patent number
US08952363B2

Reaction notes

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