Water → HCID 23449121, compound

HRID 989818Notes

Reaction equation

HRID 989818 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7].ClCCl.O.[S:15]1[CH:19]=[CH:18][N:17]2[CH:20]=[N:21][CH:22]=[C:16]12>C(=S)=S>[C:5]([C:22]1[N:21]=[CH:20][N:17]2[CH:18]=[CH:19][S:15][C:16]=12)(=[O:9])[CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 5

HCID 962WaterHCID 6344Dichloromethane2×HCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 23449121HCID 23449121, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (16.2 g) was added to a solution of 15.0 ml of isobutyryl chloride in 100 ml of carbon disulfide. A solution of 40 ml of dichloromethane in 2.50 g of imidazo[5,1-b]thiazole was added dropwise to the mixture. The mixture was stirred at room temperature for 20 hr. Dichloromethane (100 ml) was added to the reaction solution. Water (60 ml) was added dropwise thereto with stirring. The organic layer was then separated. Dichloromethane (200 ml) and 100 g of sodium carbonate were added to the aqueous layer. The mixture was stirred. The insolubles were removed by filtration, and washed with dichloromethane. The filtrate was combined with the organic layer. The combined organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:ethyl acetate=1:1) to give 2.75 g of 7-isobutyrylimidazo[5,1-b]thiazole.

Workup

  1. stirringwith stirring
  2. customThe organic layer was then separated
  3. additionDichloromethane (200 ml) and 100 g of sodium carbonate were added to the aqueous layer
  4. stirringThe mixture was stirred
  5. customThe insolubles were removed by filtration
  6. washwashed with dichloromethane
  7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under the reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (dichloromethane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6233012482e5423e8fbb95ebd8af3567
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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