p-Toluenesulfonic acid monohydrate → HCID 136335909, compound

HRID 2266465Notes

Reaction equation

HRID 2266465 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH:18]([C:22](=O)[CH3:23])[C:19](=O)[CH3:20])=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]2[N:1]=[C:22]([CH3:23])[C:18]([S:17][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=3)=[C:19]([CH3:20])[C:3]=2[C:4]([OH:9])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 7226463-[(4-Chlorophenyl)sulfanyl]pentane-2,4-dioneHCID 50700783-Amino-4-chlorophenol

Product 1

HCID 136335909HCID 136335909, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-amino-4-chlorophenol (5.0 g), 3-(4-chlorophenylsulfanyl)pentane-2,4-dione (8.4 g), p-toluenesulfonic acid monohydrate (3.20 g) and toluene (150 mL) was heated at reflux for 2 days. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and cyclohexane (1:9 by volume) gave title compound as a pale yellow solid, 0.99 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  8. washeluting with a mixture of dichloromethane and cyclohexane (1:9 by volume)

Sources & evidence

ORD record
ord-238676a12760481f81f9498a330360e3
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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