Pivaloyl chloride → HCID 23449341, compound

HRID 989812Notes

Reaction equation

HRID 989812 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].[S:12]1[CH:16]=[CH:15][N:14]2[CH:17]=[N:18][CH:19]=[C:13]12>C(=S)=S.ClCCl>[C:5]([C:19]1[N:18]=[CH:17][N:14]2[CH:15]=[CH:16][S:12][C:13]=12)(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 62493Pivaloyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 23449341HCID 23449341, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (6.0 g) was added to a solution of 6.1 ml of pivaloyl chloride in 50 ml of carbon disulfide. The mixture was stirred. A solution of 1.2 g of imidazo[5,1-b]thiazole in 20 ml of dichloromethane was added thereto, and the mixture was stirred at room temperature for 48 hr. Dichloromethane (200 ml) was added to the reaction mixture. The mixture was washed with water and a saturated aqueous sodium hydrogencarbonate solution in that order, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give 0.92 g of 7-pivaloylimidazo[5,1-b]thiazole.

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hr
  2. washThe mixture was washed with water
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution in that order, and then dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d40a513f873a4c77a369d1ef99633c84
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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