p-Toluenesulfonic acid monohydrate → HCID 22387417, compound

HRID 1072706Notes

Reaction equation

HRID 1072706 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12](=O)[CH3:13])=[CH:5][CH:4]=1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH2:25])=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 533915p-BromophenethylamineHCID 114698111-(4-Methoxyphenyl)pentane-1,4-dione

Product 1

HCID 22387417HCID 22387417, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(4-methoxyphenyl)-1,4-pentanedione (3.20 g, 15.5 mol), 2-(4-bromophenyl)ethylamine (3.74 g, 18.7 mmol) and p-toluenesulfonic acid monohydrate (150 mg, 0.871 mmol) in toluene (100 ml) was refluxed for 20 hours with heating. The insoluble matter was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 3.93 g (yield: 68.0%)

Workup

  1. temperaturewith heating
  2. filtrationThe insoluble matter was filtered out
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  5. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-2117caf8a70a4a43916850f572abca58
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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