p-Toluenesulfonic acid monohydrate → HCID 15908403, compound

HRID 396754Notes

Reaction equation

HRID 396754 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH:12]=[CH:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:29]=[CH:28][C:26]([N:27]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH3:15])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 4191105[4-(2-furyl)phenyl]amine hydrochlorideHCID 54299304HCID 54299304, compound

Product 1

HCID 15908403HCID 15908403, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[4-(methylsulfonyl)phenyl]pentene-1 4-dione (0.305 g, 1.2 mmol prepared according to the method of J. Med. Chem., 1997, 40, 1619), 4-(2-furyl)aniline (0.35 g, 2 mmol), and p-toluenesulfonic acid monohydrate (0.015 g) in toluene (40 mL) was heated at reflux temperature for 16 hours using Dean-Stark apparatus. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (4/1). The resulting solid was recrystallized from CH2Cl2/hexane to give the title compound (0.11 g, 24.3% yield).

Workup

  1. customprepared
  2. temperatureat reflux temperature for 16 hours
  3. temperatureAfter cooling
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane/ethyl acetate (4/1)
  7. customThe resulting solid was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-91780cf7a27e46949551b12c5a53c5e7
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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