1-Bromohexane → HCID 21858044, compound

HRID 1834997Notes

Reaction equation

HRID 1834997 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[C:6]([CH3:8])[N:7]=1)[CH3:2].[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>C1COCC1>[CH2:12]([N:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:3]1[CH2:1][CH3:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 178437635HCID 178437635, compound

Product 1

HCID 21858044HCID 21858044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Hexyl-2-ethyl-4-methylimidazole was prepared in the following manner. All manipulations were performed under a nitrogen atmosphere. 2-Ethyl-4-methylimidazole (1.0 g) was dissolved in 10 mL THF. Sodium hydride (0.218 g) was added as a solid. An additional 10 mL of solvent was used to wash the hydride into the flask. There was a vigorous evolution of hydrogen. Mixture was stirred at room temperature overnight. 1-Bromohexane (1.568 mL) was added all at once. Mixture was stirred over weekend at room temperature and then refluxed for several hours. Reaction mixture was cooled and then filtered through Celite 545. Solvent was stripped under vacuum to yield viscous, yellow oil. Proton NMR spectrum (E102868-78) is consistent with indicated formulation and starting 1-bromohexane. This mixture was used without purification.

Workup

  1. washto wash the hydride into the flask
  2. addition1-Bromohexane (1.568 mL) was added all at once
  3. stirringMixture was stirred over weekend at room temperature
  4. temperaturerefluxed for several hours
  5. customReaction mixture
  6. temperaturewas cooled
  7. filtrationfiltered through Celite 545
  8. customto yield viscous
  9. customThis mixture was used without purification

Sources & evidence

ORD record
ord-33516c127aea423cacacbc9f488729b2
Source dataset
uspto-grants-2004_08
Patent number
US06770122B2

Reaction notes

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