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

HRID 31540

Reaktionsgleichung

Reaktionsgleichung von HRID 31540
[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

Komponenten

4

Edukt 2

HCID 134054-Methylbenzoyl ChlorideHCID 1401461-Phenylsulfonylpyrrole

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Under nitrogen atmosphere, 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), and the mixture was allowed to stand at room temperature for 7 days. The reaction solution was washed successively with 1N aqueous hydrochloric acid solution (750 mL×2), 1N aqueous sodium hydroxide solution (750 mL) and saturated saline (100 mL), dried, and filtered. The filtrate was concentrated under atmospheric pressure until about 500 ml, and thereto was added hexane (500 mL). The reaction mixture was further concentrated until about 500 ml, cooled to 10° C., and the resulting crystals were collected by filtration. The obtained crystals were washed successively with hexane and toluene to give the title compound (315 g, 71%).

Aufarbeitung

  1. washThe reaction solution was washed successively with 1N aqueous hydrochloric acid solution (750 mL×2), 1N aqueous sodium hydroxide solution (750 mL) and saturated saline (100 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under atmospheric pressure until about 500 ml
  5. additionwas added hexane (500 mL)
  6. concentrationThe reaction mixture was further concentrated until about 500 ml
  7. filtrationthe resulting crystals were collected by filtration
  8. washThe obtained crystals were washed successively with hexane and toluene

Quellen und Nachweise

ORD-Eintrag
ord-69e667da46634917ac0f063ee4dba93a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425642B2

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