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

HRID 1883167Notes

Reaction equation

HRID 1883167 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>C(Cl)Cl>[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

Under nitrogen atmosphere, to a solution of 1-benzenesulfonyl-1H-pyrrole (283.9 g) in methylene chloride (1.0 L) were added p-toluoyl chloride (318 g) and boron trifluodie ether complex (350 g), and the mixture was allowed to stand at room temperature for 7 days. The reaction solution was washed twice with IN hydrochloric acid (750 mL), washed with 1N aqueous sodium hydroxide solution (750 mL) and a saturated brine (100 mL), dried, and filtered. The filtrate was concentrated to about a half volume thereof under atmospheric pressure, and thereto was added hexane (500 mL). The mixture was further concentrated, and methylene chloride was evaporated off. The resultant was cooled to 10° C., and the precipitated crystals were collected by filtration, washed with hexane and toluene, and dried to give (1-benzenesulfonyl-1H-pyrrol-2-yl) (4-methylphenyl) ketone (315 g, 71%).

Workup

  1. washThe reaction solution was washed twice with IN hydrochloric acid (750 mL)
  2. washwashed with 1N aqueous sodium hydroxide solution (750 mL)
  3. dry with materiala saturated brine (100 mL), dried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to about a half volume
  6. additionunder atmospheric pressure, and thereto was added hexane (500 mL)
  7. customwas evaporated off
  8. filtrationthe precipitated crystals were collected by filtration
  9. washwashed with hexane and toluene
  10. customdried

Sources & evidence

ORD record
ord-b7920fd4e5d34f9eb858a94d7a04786a
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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