Acetyl chloride → 7-Acetyl-5-methylimidazo[5,1-b]thiazole

HRID 989820Notes

Reaction equation

HRID 989820 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1[N:17]2[C:13]([S:14][CH:15]=[CH:16]2)=[CH:12][N:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(=S)=S.ClCCl>[C:5]([C:12]1[N:11]=[C:10]([CH3:9])[N:17]2[CH:16]=[CH:15][S:14][C:13]=12)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 6451240Aluminum(III) ChlorideHCID 17773803HCID 17773803, compound

Product 1

HCID 234491157-Acetyl-5-methylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (6.96 g) was added to a solution of 4.33 ml of acetyl chloride in 40 ml of carbon disulfide. A solution of 1.20 g of 5-methylimidazo[5,1-b]thiazole in 40 ml of dichloromethane was added dropwise thereto. The mixture was stirred at room temperature for 24 hr. The reaction solution was poured into 40 g of ice. Dichloromethane (100 ml) was added thereto. Sodium carbonate (32 g) was added to the mixture with stirring. The insolubles were removed by filtration, and washed with dichloromethane. The filtrate was concentrated under the reduced pressure. Ethyl acetate (20 ml) was added thereto. The resultant crystal was collected by filtration. The filtrate was purified by column chromatography on silica gel (dichloromethane:methanol=20:1). The purification product was combined with the above collected crystal to give 1.45 g of 7-acetyl-5-methylimidazo[5,1-b]thiazole.

Workup

  1. stirringwith stirring
  2. customThe insolubles were removed by filtration
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated under the reduced pressure
  5. additionEthyl acetate (20 ml) was added
  6. filtrationThe resultant crystal was collected by filtration
  7. customThe filtrate was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)
  8. customabove collected crystal

Sources & evidence

ORD record
ord-5ece6b49802a4e6a8e717adf7be2980b
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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