Hydrochloric Acid → 3-(Hydroxyaminocarbonyl)methylimidazo[5,1-b]thiazole

HRID 1603493Notes

Reaction equation

HRID 1603493 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[N:8]2[CH:14]=[N:13][CH:12]=[C:9]2[S:10][CH:11]=1)=O)C.Cl.[NH2:16][OH:17].[O-]CC.[Na+].Cl>C(O)C>[OH:17][NH:16][C:4]([CH2:6][C:7]1[N:8]2[CH:14]=[N:13][CH:12]=[C:9]2[S:10][CH:11]=1)=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 196050653-Ethoxycarbonylmethylimidazo[5,1-b]thiazole

Product 1

HCID 196050273-(Hydroxyaminocarbonyl)methylimidazo[5,1-b]thiazoleYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2 ml of an ethanol solution containing 204.3 mg of 3-ethoxycarbonylmethylimidazo[5,1-b]thiazole, 108.2 mg of hydroxylamine hydrochloride and 210.2 mg of a sodium ethoxide powder were added, and the mixture was then stirred at room temperature for 2 hours. Under ice-cooling, 0.4 ml of 1N hydrochloric acid was added to the reaction solution to neutralize the solution. The solvent was evaporated under reduced pressure, and the resulting residue was purified by Diaion HP-20 Resin to obtain 140 mg of the title compound.

Workup

  1. additionwere added
  2. temperatureUnder ice-cooling
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by Diaion HP-20 Resin

Sources & evidence

ORD record
ord-e4a0e5b1563f4d25a1527d34a8765996
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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