Acetyl chloride → 7-Acetyl-3-methylimidazo[5,1-b]thiazole

HRID 989814Notes

Reaction equation

HRID 989814 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1[N:11]2[CH:17]=[N:16][CH:15]=[C:12]2[S:13][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(=S)=S.ClCCl>[C:5]([C:15]1[N:16]=[CH:17][N:11]2[C:10]([CH3:9])=[CH:14][S:13][C:12]=12)(=[O:7])[CH3:6]

Participants

8

Reactant 5

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 6451240Aluminum(III) ChlorideHCID 22631500HCID 22631500, compound

Product 1

HCID 234491247-Acetyl-3-methylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (16.0 g) was added to a solution of 10.0 ml of acetyl chloride in 100 ml of carbon disulfide at room temperature. The mixture was stirred for 30 min. A solution of 2.76 g of 3-methylimidazo[5,1-b]thiazole in 40 ml of dichloromethane was added dropwise thereto over a period of 15 min with stirring. The mixture was further stirred for 6 hr. The reaction solution was added to a mixture of 200 ml of dichloromethane with 100 g of ice with thorough stirring. After dissolution of the ice, 40 g of sodium carbonate and 50 g of sodium sulfate were added in that order with thorough stirring. The mixture was stirred under ice cooling for 30 min. After standing, the organic layer was separated by decantation. The gum residue was extracted with dichloromethane (100 ml, five times), and then combined with the organic layer. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated to dryness under the reduced pressure. Ethyl acetate (10 ml) was added to the concentrate. The resultant solid was triturated with 10 ml of ethyl acetate, collected by filtration, and washed with a minor amount of ethyl acetate. The washed product was dried under the reduced pressure to give 2.92 g of 7-acetyl-3-methylimidazo[5,1-b]thiazole.

Workup

  1. stirringover a period of 15 min with stirring
  2. stirringThe mixture was further stirred for 6 hr
  3. additionwere added in that order with thorough stirring
  4. stirringThe mixture was stirred under ice cooling for 30 min
  5. customthe organic layer was separated by decantation
  6. extractionThe gum residue was extracted with dichloromethane (100 ml, five times)
  7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated to dryness under the reduced pressure
  9. additionEthyl acetate (10 ml) was added to the concentrate
  10. customThe resultant solid was triturated with 10 ml of ethyl acetate
  11. filtrationcollected by filtration
  12. washwashed with a minor amount of ethyl acetate
  13. customThe washed product was dried under the reduced pressure

Sources & evidence

ORD record
ord-ef968b0232174e7f9dd54c3dcb27d87a
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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