p-Toluenesulfonic acid → 1-[4-[2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-1-yl]phenyl]ethanone

HRID 1585061Notes

Reaction equation

HRID 1585061 reaction equation
[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][C:22]([C:25](=[O:27])[CH3:26])=[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][C:22]([C:25](=[O:27])[CH3:26])=[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

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7468p-AminoacetophenoneHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

Product 1

HCID 107605361-[4-[2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-1-yl]phenyl]ethanoneYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (Example 1, Step 2) (400 mg, 1.57 mmol), p-amino-acetophenone (234 mg, 1.73 mmol) and p-toluenesulfonic acid (30 mg) in toluene (40 ml) was heated to reflux for 5 hours. The reaction mixture was cooled, filtered and concentrated. The crude reddish solid (1.2 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 1-[4-[2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-1-yl]phenyl]ethanone (336 mg, 61%) as a white solid: mp 179-80° C. Anal Calc'd. for C20H19NSO3 ·0.1 H2O: C, 64.67; H, 5.70; N, 3.77; S, 8.63. Found: C, 64.68; H, 5.52; N, 3.82; S, 8.08.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude reddish solid (1.2 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-932c3e7c55e6435bacf475275f8338da
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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