Chlorosulfonic acid → 1-[(4-Methylphenyl)sulfonyl]-1H-pyrrole-3-sulfonyl chloride

HRID 1844742Notes

Reaction equation

HRID 1844742 reaction equation
[S:1]([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:16][S:17](O)(=[O:19])=[O:18]>C(#N)C>[S:1]([N:11]1[CH:15]=[CH:14][C:13]([S:17]([Cl:16])(=[O:19])=[O:18])=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 6400871-Tosylpyrrole

Product 1

HCID 862324361-[(4-Methylphenyl)sulfonyl]-1H-pyrrole-3-sulfonyl chlorideYield 20.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of compound 27a (5.0 g, 22.6 mmol) in ACN (50 mL) was carefully added ClSO3H (15.8 g, 136 mmol) and the solution was stirred at rt overnight, poured on ice-water and extracted with CHCl3 twice. The combined organic layers were washed with aq. NaHCO3 and brine (3×), concentrated and purified by CC (PE/EA=50/1) to give compound 27b (1.45 g, 20%) as a solid.

Workup

  1. additionpoured on ice-water
  2. extractionextracted with CHCl3 twice
  3. washThe combined organic layers were washed with aq. NaHCO3 and brine (3×)
  4. concentrationconcentrated
  5. custompurified by CC (PE/EA=50/1)

Sources & evidence

ORD record
ord-2e5129b24cad4f4787b6e11821da16b1
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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