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

HRID 31541

Reaction equation

HRID 31541 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:14])[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1.[C:15]1([S:21]([N:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)CCl>[C:15]1([S:21]([N:24]2[CH:25]=[CH:26][C:27]([C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH3:14])=[CH:6][CH:7]=3)=[O:12])=[CH:28]2)(=[O:23])=[O:22])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 1401461-PhenylsulfonylpyrroleHCID 6451240Aluminum(III) Chloride

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

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

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionthe aqueous layer was extracted twice with dichloromethane
  3. customdried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ba8804115d7f438d8e16948d3df34747
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Linked notes

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