Dimethylformamide → 7-Formyl-5-methylimidazo[5,1-b]thiazole

HRID 989872Notes

Reaction equation

HRID 989872 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[CH3:11][C:12]1[N:19]2[C:15]([S:16][CH:17]=[CH:18]2)=[CH:14][N:13]=1.[OH-].[Na+]>ClCCl.O>[CH:4]([C:14]1[N:13]=[C:12]([CH3:11])[N:19]2[CH:18]=[CH:17][S:16][C:15]=12)=[O:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 17773803HCID 17773803, compound

Product 1

HCID 234491637-Formyl-5-methylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

DMF (8 ml) was added to 40 ml of dichloromethane. The mixture was cooled in an argon atmosphere to 0° C. A solution of 9 ml of phosphorus oxychloride in 40 ml of dichloromethane was added dropwise thereto. Further, a solution of 1.2 g of 5-methylimidazo[5,1-b]thiazole in 20 ml of dichloromethane was added dropwise thereto. The mixture was heated under reflux for 5 hr. The reaction solution was poured into iced water, and then adjusted to pH 10 by the addition of an aqueous sodium hydroxide solution. The mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate. The solvent was then concentrated under the reduced pressure. The residue was purified by chromatography on silica gel to give 1.5 g of 7-formyl-5-methylimidazo[5,1-b]thiazole.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationThe solvent was then concentrated under the reduced pressure
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a1e606136d4044a884640198cec2c533
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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