Sodium Hydroxide → 2-Bromoimidazo[5,1-b]thiazole

HRID 1444171Notes

Reaction equation

HRID 1444171 reaction equation
[Br:1][C:2]1[S:6][C:5]2=[C:7](C(O)=O)[N:8]=[CH:9][N:4]2[CH:3]=1.[OH-].[Na+]>C(O)CO>[Br:1][C:2]1[S:6][C:5]2=[CH:7][N:8]=[CH:9][N:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 591684042-Bromoimidazo(4,3-b)(1,3)thiazole-7-carboxylic acid

Product 1

HCID 104654682-Bromoimidazo[5,1-b]thiazoleYield 49.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 2-bromoimidazo[5,1-b]thiazole-7-carboxylic acid (28 mg, 0.11 mmol) in ethylene glycol (1 ml) was stirred at 180° C. for 2.5 hr. The reaction solution was allowed to cool to room temperature, a 2.7 M aqueous solution (5 ml) of sodium hydroxide was added to the cooled solution, and the mixture was extracted with ethyl acetate (5 ml×3). The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure to give 2-bromoimidazo[5,1-b]thiazole (11 mg, 48%) as a crude product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (5 ml×3)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-2569992b85f94ea9b6c56f9274a54719
Source dataset
uspto-grants-2010_02
Patent number
US07662841B2

Reaction notes

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