Dimethylformamide → HCID 86762533, compound

HRID 1621350Notes

Reaction equation

HRID 1621350 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[CH2:13]([CH:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][I:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CN(C=O)C>C(#N)C>[I-:21].[CH2:13]([CH:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][N+:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][NH+:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[I-:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 111074,4'-BipyridineHCID 580983237-(Iodomethyl)pentadecane

Product 1

HCID 86762533HCID 86762533, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen atmosphere, to a reaction vessel, 499 mg (3.19 mmol) of 4,4′-bipyridyl, 1.496 g (4.25 mmol, 1.3 eq) of 2-hexyl-1-iododecane, 10 mL of N,N′-dimethylformamide, and 40 mL of acetonitrile were added. The whole was stirred for 30 minutes at room temperature, and subsequently refluxed at 60° C. for 2 days. The reaction mixture was allowed to reach room temperature, and then the solvent was removed by evaporation. The procedure in which the residue was dissolved in a small amount of THF, reprecipitated with hexane and the precipitate was filtered under reduced pressure, was repeated twice to give 61 mg (120 μmol) of [1-(2-hexyldecyl)-4,4′-bipyridinium]iodide as a yellow solid (yield: 4%).

Workup

  1. temperaturesubsequently refluxed at 60° C. for 2 days
  2. customto reach room temperature
  3. customthe solvent was removed by evaporation
  4. dissolutionThe procedure in which the residue was dissolved in a small amount of THF
  5. customreprecipitated with hexane
  6. filtrationthe precipitate was filtered under reduced pressure

Sources & evidence

ORD record
ord-d25ee58ca9074e27ba6df589366d5e5b
Source dataset
uspto-grants-2014_07
Patent number
US08773745B2

Reaction notes

Loading…