Chlorosulfonic acid → HCID 23445312, compound

HRID 2270583Notes

Reaction equation

HRID 2270583 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 1 N 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 1 N 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-2692de30b44c43cead2c1dfa2f52f572
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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