Water → 7-Chlorosulfonylimidazo[5,1-b]thiazole

HRID 989841Notes

Reaction equation

HRID 989841 reaction equation
[S:1]([Cl:5])(=O)(=[O:3])[OH:2].[S:6]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]12.O>C(Cl)(Cl)(Cl)Cl>[Cl:5][S:1]([C:13]1[N:12]=[CH:11][N:8]2[CH:9]=[CH:10][S:6][C:7]=12)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 234490387-Chlorosulfonylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of chlorosulfuric acid in 20 ml of carbon tetrachloride was added under ice cooling to a solution of 11.18 g of imidazo[5,1-b]thiazole in 200 ml of carbon tetrachloride. The reaction mixture was heated under reflux for 6 hr. Water was added thereto under ice cooling to terminate the reaction. The mixture was extracted with dichloromethane. The organic layers were combined together. The combined organic layers were washed with a dilute aqueous sodium hydroxide solution and saturated brine in that order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. Isopropyl ether was added to the residue. The resultant powder was collected by filtration to give 4.01 g of 7-chlorosulfonylimidazo[5,1-b]thiazole.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 hr
  3. customunder ice cooling to terminate
  4. customthe reaction
  5. extractionThe mixture was extracted with dichloromethane
  6. washThe combined organic layers were washed with a dilute aqueous sodium hydroxide solution and saturated brine in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation
  9. additionIsopropyl ether was added to the residue
  10. filtrationThe resultant powder was collected by filtration

Sources & evidence

ORD record
ord-3f4beff91754427eb91d3d7c560bbe6e
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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