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Potassium Hydroxide → 1-Dodecyl-2-(2-pyridyl)imidazole

HRID 223771
Notes
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Reaction equation

HRID 223771 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.[OH-].[K+].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].ICCCCCCCCCC>C(#N)C>[CH2:26]([N:11]1[CH:10]=[CH:9][N:8]=[C:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 163141-IododecaneHCID 202821-IodododecaneHCID 5893132-(1H-imidazol-2-yl)pyridine

Product 1

HCID 205207631-Dodecyl-2-(2-pyridyl)imidazoleYield 103.7%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of 14.5 g (0.1 mole) 2-(2-pyridyl)imidazole, 6 g (0.11 mole) ground KOH, 30 g (0.1 mole) iodododecane in about 150 ml of acetonitrile was stirred and refluxed for about 2 hours. The iododecane gradually went into solution as the reaction proceeded. After the 2 hours the reaction mixture was cooled and filtered. The resulting residue was extracted with hexane to give 32.5 g of crude product.

Workup

  1. temperaturerefluxed for about 2 hours
  2. temperatureAfter the 2 hours the reaction mixture was cooled
  3. filtrationfiltered
  4. extractionThe resulting residue was extracted with hexane

Sources & evidence

ORD record
ord-71aaab8d01e14499bd40051edaaf5053
Source dataset
uspto-grants-1982_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04356309

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes