HCID 18359981, compound → 7-Ethylimidazo[5,1-b]thiazole

HRID 382600Notes

Reaction equation

HRID 382600 reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12)=[CH2:2].[H][H]>C(O)C.O.[Pd]>[CH2:1]([C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12)[CH3:2]

Participants

6

Reactant 2

HCID 18359981HCID 18359981, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 183599807-Ethylimidazo[5,1-b]thiazoleYield 25.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5.0 g of 7-vinylimidazo[5,1-b]thiazole in 40 ml of ethanol and 8 ml of water was added 2.0 g of 10% Pd-C, and the mixture was stirred under the atmosphere of hydrogen at room temperature overnight. The catalyst was removed by filtration, and the filtrate was concentrated to a small volume. The concentrate was diluted with 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and extracted with 100 ml of ethyl acetate. The organic layer was washed with aqueous saline and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:ethyl acetate=3:2) to give 1.27 g of 7-ethylimidazo[5,1-b]thiazole.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to a small volume
  3. additionThe concentrate was diluted with 10 ml of a saturated aqueous sodium hydrogen carbonate solution
  4. extractionextracted with 100 ml of ethyl acetate
  5. washThe organic layer was washed with aqueous saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography on silica gel (dichloromethane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-3ef1f47a094c4f71b1002690a220349d
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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