4-Toluenesulfonyl chloride → 7-p-Toluenesulfonylimidazo[5,1-b]thiazole

HRID 989827Notes

Reaction equation

HRID 989827 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[S:16]1[CH:20]=[CH:19][N:18]2[CH:21]=[N:22][CH:23]=[C:17]12.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([C:23]2[N:22]=[CH:21][N:18]3[CH:19]=[CH:20][S:16][C:17]=23)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 6451240Aluminum(III) ChlorideHCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 234492047-p-Toluenesulfonylimidazo[5,1-b]thiazoleYield 14.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 23.9 g of p-toluenesulfonyl chloride in 100 ml of dichloromethane was cooled to ice temperature in an argon atmosphere. Aluminum chloride (15.3 g) was added thereto. The mixture was stirred for 10 min. A solution of 3.15 g of imidazo[5,1-b]thiazole in 25 ml of dichloromethane was added dropwise thereto. The mixture was stirred for 22 hr. Dichloromethane (200 ml), 70 ml of water, and 75 g of a sodium carbonate powder were added thereto, followed by extraction. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure to give 995 mg of 7-p-toluenesulfonylimidazo[5,1-b]thiazole.

Workup

  1. stirringThe mixture was stirred for 22 hr
  2. extractionfollowed by extraction
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-89fb5cb308d247cfa4a79300e1fe55df
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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