Chlorosulfonic acid → 4-(1H-Imidazol-1-yl)benzenesulfonyl chloride

HRID 1589011Notes

Reaction equation

HRID 1589011 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]1([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[N:12]1([C:6]2[CH:11]=[CH:10][C:9]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:8][CH:7]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 815951-Phenylimidazole

Product 1

HCID 149988304-(1H-Imidazol-1-yl)benzenesulfonyl chloride

Procedure

To chlorosulfonic acid cooled to 0° C. in an ice bath is added portionwise 1-phenyl-1H-imidazole. Monitor the progress of the reaction by thin-layer chromatography. When the reaction is complete, quench the mixture on ice. Saturated aqueous NaHCO3 is added until the solution is no longer acidic. Extract the mixture with CH2Cl2. Dry the organic layer over anhydrous Na2SO4 and remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customquench the mixture on ice
  3. additionSaturated aqueous NaHCO3 is added until the solution
  4. extractionExtract the mixture with CH2Cl2
  5. dry with materialDry the organic layer over anhydrous Na2SO4
  6. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-b87b3582445646d2bed68def2858c647
Source dataset
uspto-grants-1993_06
Patent number
US05223623

Reaction notes

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