p-Toluenesulfonic acid → HCID 10425834, compound

HRID 1585063Notes

Reaction equation

HRID 1585063 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=O.[CH3:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[N:25]([C:24]3[CH:23]=[CH:22][C:21]([S:18]([CH3:17])(=[O:20])=[O:19])=[CH:27][CH:26]=3)[CH:2]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 796174-(Methylsulfonyl)anilineHCID 27586963-(1,3-Dioxolan-2-yl)-1-(4-fluorophenyl)-1-propanone

Product 1

HCID 10425834HCID 10425834, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the ketone (Step 2) (448 mg, 2 mmol), 4-(methylsulfonyl)aniline (380 mg, 2.2 mmol) and p-toluenesulfonic acid (30 mg) in toluene (40 ml) was heated to reflux for 18 hours. The reaction was cooled, filtered and concentrated. The crude solid (750 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give 2-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-pyrrole (310 mg, 55%) as a white solid: mp (DSC) 201° C. Anal Calc'd. for C17H14NSFO2 ·0.2 H2O: C, 64.01; H, 4.55; N, 4.39; S, 10.05. Found: C, 64.18; H, 4.33; N, 4.32; S, 10.36.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid (750 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-0d89e49363a64769bedf1b7368e05842
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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