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

HRID 2113288Notes

Reaction equation

HRID 2113288 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[Br:11][C:12]1[S:16][C:15]2=[CH:17][N:18]=[CH:19][N:14]2[CH:13]=1.[OH-].[Na+]>C(Cl)Cl.O>[Br:11][C:12]1[S:16][C:15]2=[C:17]([CH:3]=[O:4])[N:18]=[CH:19][N:14]2[CH:13]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 104654682-Bromoimidazo[5,1-b]thiazole

Product 1

HCID 115287442-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Dimethylformamide (0.13 ml) and 0.15 ml of phosphorus oxychloride were added in that order to a solution of 300 mg of 2-bromoimidazo[5,1-b]thiazole in 3 ml of methylene chloride under an argon atmosphere, and the mixture was stirred at 80° C. for 6 hr. Water was added to the reaction mixture to stop the reaction, and the reaction mixture was adjusted to pH 10 by the addition of a 1 N aqueous sodium hydroxide solution. The reaction mixture was then extracted with ethyl acetate, and the organic layer was then washed with saturated brine and was dried over magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:10) to give 223 mg of 2-bromo-7-formylimidazo[5,1-b]thiazole.

Workup

  1. customthe reaction
  2. extractionThe reaction mixture was then extracted with ethyl acetate
  3. washthe organic layer was then washed with saturated brine
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:10)

Sources & evidence

ORD record
ord-d2e1590f99fb490b80e1278371878f20
Source dataset
uspto-grants-2009_04
Patent number
US07524951B2

Reaction notes

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