2-Bromo-7-hydroxymethylimidazo[5,1-b]thiazole → 2-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

HRID 1444188Notes

Reaction equation

HRID 1444188 reaction equation
[Br:1][C:2]1[S:6][C:5]2=[C:7]([CH2:10][OH:11])[N:8]=[CH:9][N:4]2[CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[S:6][C:5]2=[C:7]([CH:10]=[O:11])[N:8]=[CH:9][N:4]2[CH:3]=1

Participants

4

Reactant 1

HCID 591684062-Bromo-7-hydroxymethylimidazo[5,1-b]thiazole

Product 1

HCID 115287442-Bromoimidazo[5,1-b]thiazole-7-carbaldehydeYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (content 75%; 5.3 g, 46.11 mmol) was added to a solution of 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (1.1 g, 4.61 mmol) in dichloromethane (100 ml), and the mixture was heated under reflux for 30 min. After the completion of the reaction, the reaction mixture was filtered through Celite, followed by washing with dichloromethane. The solvent was then removed by distillation under the reduced pressure to give 2-bromoimidazo[5,1-b]thiazole-7-carbaldehyde (989 mg, 93%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customAfter the completion of the reaction
  4. filtrationthe reaction mixture was filtered through Celite
  5. washby washing with dichloromethane
  6. customThe solvent was then removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-8533ad675ef4474994779d7fa014f959
Source dataset
uspto-grants-2010_02
Patent number
US07662841B2

Reaction notes

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