2-Mercaptoethanol → HCID 19854391, compound

HRID 1649754Notes

Reaction equation

HRID 1649754 reaction equation
[OH:1][CH2:2][CH2:3][SH:4].[H-].[Na+].Cl[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[N:13]=1>C(O)C>[OH:1][CH2:2][CH2:3][S:4][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[N:13]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-

Product 1

HCID 19854391HCID 19854391, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of ethanol is suspended 1.46 g of 2-hydroxyethylmercaptan. With ice-cooling, 897 mg of sodium hydride (oily, 60 wt.%) is added and the mixture is stirred for 10 minutes. Then, 1.91 g of 6-chloroimidazo[1,2-b]pyridazine is added and the mixture is stirred at room temperature for 6 hours. The solvent is distilled off under reduced pressure and the residue is shaken well with dichloromethane and water. The dichloromethane layer is separated and dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The residue is subjected to silica gel (200 g) column chromatography and after the column is washed with ethyl acetate, elution is carried out with acetone. The fractions rich in the desired compound are pooled and the solvent is distilled off under reduced pressure. To the residue are added dichloromethane and isopropyl ether and the resulting pale-brown powder is collected by filtration. This procedure gives 500 mg of 6-(2-hydroxyethylthio)imidazo[1,2-b]pyridazine.

Workup

  1. temperatureWith ice-cooling
  2. stirringthe mixture is stirred at room temperature for 6 hours
  3. distillationThe solvent is distilled off under reduced pressure
  4. stirringthe residue is shaken well with dichloromethane and water
  5. customThe dichloromethane layer is separated
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. washafter the column is washed with ethyl acetate, elution
  9. distillationthe solvent is distilled off under reduced pressure
  10. additionTo the residue are added dichloromethane and isopropyl ether
  11. filtrationthe resulting pale-brown powder is collected by filtration

Sources & evidence

ORD record
ord-bd56f247cf734ad9975094e7746aed09
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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