Chlorosulfonic acid → HCID 23445312, compound

HRID 234309Notes

Reaction equation

HRID 234309 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[CH:18][CH:17]=[CH:16]2)=[CH:11][CH:10]=1)([CH3:8])[CH3:7]>C(Cl)(Cl)Cl>[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[CH:18][CH:17]=[C:16]2[S:2]([OH:5])(=[O:4])=[O:3])=[CH:11][CH:10]=1)([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 4105194HCID 4105194, compound

Product 1

HCID 23445312HCID 23445312, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (1.82 ml, 27.08 mmol) was slowly added to a solution of 1-(4'-isopropylphenyl)pyrrole (5.01 g, 27.08 mmol) in chloroform (100 ml) at 0° C. The resulting solution was stirred at 0° C. for 1 h and for an additional 1 h at room temperature. Chloroform was removed under reduced pressure. The resultant brown liquid was diluted with ethyl acetate (200 ml) and washed with 1N sodium hydroxide. The aqueous layer was then acidified with concentrated hydrochloric acid (pH<1) and then extracted with chloroform (2×150 ml). The combined organic layers was dried over magnesium sulfate and was filtered. Removal of the solvent gave 1-(4'-isopropylphenyl)pyrrole-2-sulfonic acid as a brown syrup (3 g, 42 % yield).

Workup

  1. customChloroform was removed under reduced pressure
  2. additionThe resultant brown liquid was diluted with ethyl acetate (200 ml)
  3. washwashed with 1N sodium hydroxide
  4. extractionextracted with chloroform (2×150 ml)
  5. dry with materialThe combined organic layers was dried over magnesium sulfate
  6. filtrationwas filtered
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-051309c3a0c74a8281546cd358a34f90
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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