Ethanol → HCID 19907431, compound

HRID 2371557Notes

Reaction equation

HRID 2371557 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH3:2].[CH2:29]([I:31])[CH3:30].C[I:33].[CH2:34](O)[CH3:35]>>[I-:31].[I-:33].[CH2:25]([N+:22]([CH2:29][CH3:30])([CH2:23][CH3:24])[CH2:21][CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][CH2:4][N+:3]([CH2:34][CH3:35])([CH2:1][CH3:2])[CH2:27][CH3:28])=[CH:8][CH:9]=2)=[CH:18][CH:17]=1)[CH3:26]

Participants

5

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 6340IodoethaneHCID 19907437HCID 19907437, compound

Product 1

HCID 19907431HCID 19907431, compound

Procedure

To a solution of 400 mg of 4,4'-bis(3-diethylaminopropyl)biphenyl in 4 ml of ethanol was added 0.84 ml of ethyl iodide, and the mixture was refluxed for 3 hours. After adding further 0.42 ml of methyl iodide, the mixture was refluxed for 2 hours and concentrated under a reduced pressure. To the concentrate were added 5 ml of acetone and 50 ml of ethyl acetate. The resulting crystal was collected by filtration, washed with ethanol, acetone and n-hexane, and dried under a reduced pressure. The obtained pale yellow powder was recrystallized from 10 ml of ethanol to obtain 475 mg of the title compound as a pale yellow crystal.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperaturethe mixture was refluxed for 2 hours
  3. concentrationconcentrated under a reduced pressure
  4. additionTo the concentrate were added 5 ml of acetone and 50 ml of ethyl acetate
  5. filtrationThe resulting crystal was collected by filtration
  6. washwashed with ethanol, acetone and n-hexane
  7. customdried under a reduced pressure
  8. customThe obtained pale yellow powder was recrystallized from 10 ml of ethanol

Sources & evidence

ORD record
ord-8190d5fd580a4ab5a575dd3d263fefef
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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