p-Toluenesulfonic acid → HCID 44515178, compound

HRID 638801Notes

Reaction equation

HRID 638801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH2:12][CH3:13])=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([N:21]2[C:11]([CH2:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 78124-ChloroanilineHCID 145291851-(4-Chlorophenyl)hexane-1,4-dione

Product 1

HCID 44515178HCID 44515178, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-chlorophenyl)hexane-1,4-dione (2.10 g, 9.35 mmol, as obtained in Step-1), 4-chloro aniline (1.31 g, 10.29 mmol), and p-toluene sulfonic acid (0.321 g, 1.80 mmol) in toluene (5.0 ml) was refluxed over molecular sieves or using a Dean Stark apparatus. The progress of the reaction was monitored by TLC and after three hours, toluene was removed under reduced pressure. The residue was dissolved in ethyl acetate (200 ml), washed with aqueous sodium bicarbonate solution (2×75 ml), followed by washing with water (2×50 ml) and brine (1×25 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent evaporated off. The solid so obtained was washed with hexane to give 2.39 g (81%) of the title compound.

Workup

  1. temperaturewas refluxed over molecular sieves
  2. customtoluene was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  4. washwashed with aqueous sodium bicarbonate solution (2×75 ml)
  5. washby washing with water (2×50 ml) and brine (1×25 ml)
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. customthe solvent evaporated off
  8. customThe solid so obtained
  9. washwas washed with hexane

Sources & evidence

ORD record
ord-56f11aaa8d8c4d4189edc9df050a6917
Source dataset
uspto-grants-2010_04
Patent number
US07691837B2

Reaction notes

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