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

HRID 505668Notes

Reaction equation

HRID 505668 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH3:24])[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1>ClCCl>[CH3:24][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:14]2[N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH:11]=[CH:12][CH:13]=2)=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 1401461-Phenylsulfonylpyrrole

Product 1

HCID 22928710(1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketoneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 1-benzenesulfonyl-1H-pyrrole (284 g, 1.37 mol) in dichloromethane (1.0 L) were added p-toluoyl chloride (318 g, 2.06 mol) and boron trifluoride ether complex (350 g, 2.47 mol) in a stream of nitrogen and the mixture was allowed to stand for 7 hours at room temperature. The reaction mixture was washed with 1N aqueous hydrochloric acid solution (750 mL) twice, 1N aqueous sodium hydroxide solution (750 mL) and saturated brine (100 mL) successively, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure so that the volume became about 500 ml and thereto was added hexane (500 mL). Further the mixture was concentrated so that the volume became about 500 ml, and cooled to 10° C. and resulting crystals were collected by filtration. The crystals were washed with hexane and then toluene and dried to give the subject compound (315 g, 71%).

Workup

  1. washThe reaction mixture was washed with 1N aqueous hydrochloric acid solution (750 mL) twice
  2. dry with material1N aqueous sodium hydroxide solution (750 mL) and saturated brine (100 mL) successively, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure so that the volume
  5. additionwas added hexane (500 mL)
  6. concentrationFurther the mixture was concentrated so that the volume
  7. customresulting crystals
  8. filtrationwere collected by filtration
  9. washThe crystals were washed with hexane
  10. dry with materialtoluene and dried

Sources & evidence

ORD record
ord-a6f9fc0ebfb848e8b4afe0b3a098c7aa
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

Loading…