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

HRID 1352843Notes

Reaction equation

HRID 1352843 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[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:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=3)=[O:8])=[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

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

Workup

  1. extractionthe aqueous layer was extracted with dicloromethane twice
  2. customdried
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-d217a5c5d38b453d806743449fc20ea4
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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