Benzoyl chloride → 7-Benzoylimidazo[5,1-b]thiazole

HRID 989833Notes

Reaction equation

HRID 989833 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[S:14]1[CH:18]=[CH:17][N:16]2[CH:19]=[N:20][CH:21]=[C:15]12.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(=S)=S.ClCCl>[C:5]([C:21]1[N:20]=[CH:19][N:16]2[CH:17]=[CH:18][S:14][C:15]=12)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 6451240Aluminum(III) ChlorideHCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 226320567-Benzoylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (5.33 g) was added to a solution of 4.64 ml of benzoyl chloride in 50 ml of carbon disulfide. A solution of 1.24 g of imidazo[5,1-b]thiazole in 50 ml of dichloromethane was added dropwise thereto. The mixture was stirred at room temperature for 2 hr. The reaction solution was poured into 50 g of ice. Dichloromethane (100 ml) was added thereto. Sodium carbonate (16.7 g) and 16.7 g of sodium sulfate were added in that order to the mixture with stirring. The insolubles were removed by filtration through Celite, and then washed with dichloromethane. Filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to dichloromethane:ethyl acetate=2:1) to give 1.39 g of 7-benzoylimidazo[5,1-b]thiazole.

Workup

  1. stirringwith stirring
  2. customThe insolubles were removed by filtration through Celite
  3. washwashed with dichloromethane
  4. concentrationFiltrate was concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to dichloromethane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4df208c0b2214a6ba60b4c28c35a3437
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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