Hydrochloric Acid → 2-Bromoimidazo[5,1-b]thiazole

HRID 1444181Notes

Reaction equation

HRID 1444181 reaction equation
Cl.[Br:2][C:3]1[S:7][C:6]2=[C:8](C(OC)=O)[N:9]=[CH:10][N:5]2[CH:4]=1.[OH-].[Na+]>C(O)(=O)CC>[Br:2][C:3]1[S:7][C:6]2=[CH:8][N:9]=[CH:10][N:5]2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59168410Methyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate

Product 1

HCID 104654682-Bromoimidazo[5,1-b]thiazoleYield 28.1%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

Concentrated hydrochloric acid (0.3 ml) was added to a solution of methyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate (54 mg, 0.21 mmol) in propionic acid (2 ml), and the mixture was heated under reflux for 11 hr. The reaction solution was neutralized with a 2 M aqueous solution of sodium hydroxide and was extracted with ethyl acetate (7 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. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give 2-bromoimidazo[5,1-b]thiazole (12 mg, 28%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 11 hr
  3. extractionwas extracted with ethyl acetate (7 ml×3)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-0cc0acd0af4740368a8d8675e0666591
Source dataset
uspto-grants-2010_02
Patent number
US07662841B2

Reaction notes

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