p-Toluenesulfonic acid → 1-Phenyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

HRID 1585057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585057
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

Produkt 1

HCID 108050031-Phenyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrroleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (Example 1, step 2) (300 mg, 1.18 mmol), aniline (0.12 ml, 1.3 mmol) and p-toluenesulfonic acid (25 mg) in toluene (50 ml) was heated to reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude brownish solid (420 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 2-methyl-5-[4-(methylsulfonyl)phenyl]-1-phenyl-1H-pyrrole (305 mg, 83%) as a white solid: mp (DSC) 148° C. Anal Calc'd. for C18H17NSO2 : C, 69.43; H, 5.50; N, 4.50; S, 10.30. Found: C, 69.18; H, 5.42; N, 4.42; S, 10.06.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude brownish solid (420 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-8f56d9c5a2ad412f86694c26b856ea36
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05935990

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