Ethanol → N-(p-decylphenyl)-2,4,6-trimethylpyridinium bisulfate

HRID 359307Notes

Reaction equation

HRID 359307 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[O-:2].[C:6]1([C:12]2[CH:17]=[C:16](C3C=CC=CC=3)C=C(C3C=CC=CC=3)[O+]=2)[CH:11]=C[CH:9]=[CH:8][CH:7]=1.C(O)C.[CH2:33]([C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].NC1C=CC=CC=1>C(#N)C>[S:1](=[O:3])(=[O:2])([OH:5])[O-:4].[CH2:33]([C:43]1[CH:44]=[CH:45][C:46]([N+:47]2[C:17]([CH3:16])=[CH:12][C:6]([CH3:11])=[CH:7][C:8]=2[CH3:9])=[CH:48][CH:49]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 702EthanolHCID 6115AnilineHCID 923094-DecylanilineHCID 117291982,4,6-Triphenylpyrylium Hydrogensulfate

Product 1

HCID 20064834N-(p-decylphenyl)-2,4,6-trimethylpyridinium bisulfate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 500-ml round-bottom flask is placed 2.03 g (0.005 mole) of 2,4,6-triphenylpyrylium bisulfate. To this is added 150 ml of ethanol followed by 2.34 g (0.01 mole) of p-decylaniline. This mixture is refluxed for about 8 hours and allowed to cool. A quantity of the starting aniline precipitates and is removed by filtration. The ethanol is then removed to give a yellow waxy material which is washed with ether to give a white powder. This material is then dissolved in acetonitrile to cause the remaining aniline to precipitate. The acetonitrile is removed to give the desired product which is then rinsed with ether to remove any residual acetonitrile. The yield is 1.77 g (0.0028 mole) of 2,4,6-triphenylpyridinium bisulfate as confirmed by nuclear magnetic resonance (1H) and elemental analysis.

Workup

  1. customIn a 500-ml round-bottom flask is placed
  2. temperatureThis mixture is refluxed for about 8 hours
  3. temperatureto cool
  4. customA quantity of the starting aniline precipitates
  5. customis removed by filtration
  6. customThe ethanol is then removed
  7. customto give a yellow waxy material which
  8. washis washed with ether
  9. customto give a white powder
  10. customto precipitate
  11. customThe acetonitrile is removed

Sources & evidence

ORD record
ord-0f057dba14024ceeb06823a8c601e54b
Source dataset
uspto-grants-1991_03
Patent number
US05000873

Reaction notes

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