Sodium Carbonate → HCID 23449259, compound

HRID 1839273Notes

Reaction equation

HRID 1839273 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[S:10]1[CH:14]=[CH:13][N:12]2[CH:15]=[N:16][CH:17]=[C:11]12.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(=S)=S.ClCCl>[C:5]([C:17]1[N:16]=[CH:15][N:12]2[CH:13]=[CH:14][S:10][C:11]=12)(=[O:8])[CH2:6][CH3:7]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 62324Propionyl chloride2×HCID 6451240Aluminum(III) Chloride2×HCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 23449259HCID 23449259, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (16.0 g) was added to a solution of 12.1 ml of propionyl chloride in 100 ml of carbon disulfide. A solution of 2.48 g of imidazo[5,1-b]thiazole in 100 ml of dichloromethane was added dropwise thereto. The mixture was stirred at room temperature for 18 hr. Propionyl chloride (12.1 ml) and 16.0 g of aluminum chloride were further added thereto, followed by stirring for 24 hr. The reaction solution was poured into 100 g of ice. Dichloromethane (200 ml) was added thereto. Sodium carbonate (100 g) and sodium sulfate (100 g) were added in that order 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 (10 ml) was added to the concentrate. The crystals thus formed were collected by filtration. The filtrate was purified by column chromatography on silica gel (dichloromethane:ethyl acetate=1:1), and then combined with the collected crystals to obtain 2.49 g of 7-propionylimidazo[5,1-b]thiazole.

Workup

  1. stirringby stirring for 24 hr
  2. stirringwith stirring
  3. customThe insolubles were removed by filtration
  4. washwashed with dichloromethane
  5. concentrationThe filtrate was concentrated under the reduced pressure
  6. additionEthyl acetate (10 ml) was added to the concentrate
  7. customThe crystals thus formed
  8. filtrationwere collected by filtration
  9. customThe filtrate was purified by column chromatography on silica gel (dichloromethane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e145c47f593c408283cd81e8a63a4fb2
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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