O-methylhydroxylammonium chloride → 7-Methoxyiminomethylimidazo[5,1-b]thiazole

HRID 382602Notes

Reaction equation

HRID 382602 reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12)=O.[CH3:11][O:12][NH3+:13].[Cl-].[OH-].[Na+]>C(O)C>[CH3:11][O:12][N:13]=[CH:1][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12

Participants

5

Reactant 3

HCID 11639O-methylhydroxylammonium chlorideHCID 14798Sodium HydroxideHCID 22390357Imidazo(4,3-b)(1,3)thiazole-7-carbaldehyde

Product 1

HCID 740532977-Methoxyiminomethylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 249 mg of 7-formylimidazo[5,1-b]thiazole in 10 ml of ethanol were added 219 mg of o-methylhydroxylamine hydrochloride and 2.67 ml of a 1N sodium hydroxide solution. The reaction mixture was stirred at room temperature for 20 hours, concentrated, then diluted with 50 ml of water, and extracted with dichloromethane. The organic layer was 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=1:1) to give 7-methoxyiminomethylimidazo[5,1-b]thiazole (low polar geometrical isomer) in a yield of 164 mg from the low polarity fraction.

Workup

  1. concentrationconcentrated
  2. additiondiluted with 50 ml of water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography on silica gel (dichloromethane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e406e0300e55466b9d6e6591718c32cf
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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