Chloride → 1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methanone

HRID 505678Notes

Reaction equation

HRID 505678 reaction equation
[Cl-].[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[C:12]1([S:18]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)CCl>[C:12]1([S:18]([N:21]2[CH:22]=[CH:23][C:24]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:11])=[CH:3][CH:4]=3)=[O:9])=[CH:25]2)(=[O:20])=[O:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 134054-Methylbenzoyl ChlorideHCID 1401461-Phenylsulfonylpyrrole

Product 1

HCID 4756391-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methanoneYield 105.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

To a suspension of alminium chloride (4.62 g, 34.7 mmol) in ethylene chloride (50 mL) was added under a nitrogen atmosphere p-toluoyl chloride (4.91 g, 31.8 mmol) in ethylene chloride (5 mL) at room temperature in a period of 10 minutes. After stirring for 30 minutes to the mixture was added 1-benzenesulfonyl-1H-pyrrole (6.00 g, 28.9 mmol) in ethylene chloride (10 mL) in a period of 10 minutes. After stirring for 2 hours at room temperature, the reaction mixture was poured into ice water and the aqueous layer was extracted twice with dichloromethane. The organic layer combined was dried over magnesium sulfate and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give the subject compound (9.9 g, 100%).

Workup

  1. stirringAfter stirring for 2 hours at room temperature
  2. extractionthe aqueous layer was extracted twice with dichloromethane
  3. dry with materialThe organic layer combined was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d6550d82281349b0a3a5a57c675912f1
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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