p-Toluenesulfonic acid → HCID 15428634, compound

HRID 1585071Notes

Reaction equation

HRID 1585071 reaction equation
O=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[CH2:3][C:4](=O)[CH2:5][CH3:6].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:5]([CH3:6])=[CH:4][CH:3]=[C:2]2[C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 97314-FluoroanilineHCID 21221418HCID 21221418, compound

Product 1

HCID 15428634HCID 15428634, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(1,3-dioxopentyl)benzenesulfonamide (160 mg, 0.63 mmol) of (Step 5), 4-fluoroaniline (65 μl, 0.69 mmol) and p-toluenesulfonic acid (6.7 mg) in toluene (25 ml) was heated at reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude mixture (820 mg) was purified by chromatography (silica gel, toluene/ethyl acetate, 8/2) to give 4-[1-(4-fluorophenyl)-5-methyl-1H-pyrrol-2-yl]benzenesulfonamide (92 mg, 45%) as a white solid: mp 147-48° C. Anal Calc'd. for C17H15N2FSO2 : C, 61.14; H, 4.65; N, 8.39; S, 9.60. Found: C, 61.34; H, 4.70; N, 8.21; S, 9.63.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture (820 mg) was purified by chromatography (silica gel, toluene/ethyl acetate, 8/2)

Sources & evidence

ORD record
ord-a32e593da3f64ce08c4410a8e4672006
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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