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

HRID 1839337Notes

Reaction equation

HRID 1839337 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-d7fd5659e1fc4163b067732ec61f978f
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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