4-Methylbenzoyl Chloride → (1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketone

HRID 1883168Notes

Reaction equation

HRID 1883168 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>ClC(Cl)C>[CH3:14][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:25]2[N:24]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:22])=[O:23])[CH:28]=[CH:27][CH:26]=2)=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

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

Product 1

HCID 22928710(1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketoneYield 105.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

Under nitrogen atmosphere, to a suspension of aluminum chloride (4.62 g) in dichloroethane (50 mL) was added a solution of p-toluoyl chloride (4.91 g) in dichloroethane (5 mL) at room temperature over a period of 10 minutes. After stirring for 30 minutes, to the mixture was added a solution of 1-benzenesulfonyl-1H-pyrrole (6.00 g) in dichloroethane (10 mL) over a period of 10 minutes. The mixture was stirred at room temperature for 2 hours, and the reaction mixture was poured into ice water, and the aqueous layer was extracted twice with methylene chloride. The organic layers were combined, dried, filtered and concentrated. The residue was purified by silica gel column chromatography to give (1-benzenesulfonyl-1H-pyrrol-2-yl) (4- methyl-phenyl) ketone (9.9 g, 100%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionthe aqueous layer was extracted twice with methylene chloride
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d334bf9696304121b91235b0e4a831c7
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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