1-Methylimidazole → HCID 178443378, compound

HRID 2208651Notes

Reaction equation

HRID 2208651 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[Br-:7].[CH2:8]([N+:4]1[CH:5]=[CH:6][N:2]([CH3:1])[CH:3]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 13901-MethylimidazoleHCID 81731-Bromodecane

Product 1

HCID 178443378HCID 178443378, compoundYield 95.8%

Conditions

Temperature
90 °C

Procedure

A 35 mL glass pressure tube (Ace Glass Cat#8648-07) containing a stir bar was charged with 4.105 g (0.050 moles) of 1-methylimdazole followed by 11.059 g (0.050 moles) of 1-bromodecane. The tube was sealed with a threaded Teflon plug and an O-ring and the tubes were placed in an oil bath on a VWR stirring hot plate. The temperature was raised to 90° C. and maintained at this temperature for 16 hours during which time the solution became viscous and the stir bar had stopped. The tube was removed from the bath and mixed vigorously on a vortexing mixer to completely mix the two layers and the tube replaced into the oil bath at 90° C. and the temperature raised to 100° C. The tube was heated for another hour and then mixed vigorously a second time followed by another hour of heating at 100° C. The cycle was repeated once more until the viscous liquid was homogeneous. The liquid was extracted with equal volumes of ethyl acetate three times followed by rotary evaporation to remove the residual ethyl acetate to give 14.532 g of the 1-hexyl-3-methylimidazolium bromide as a viscous lightly yellow colored oil. Compound is also available from IoLiTec (Heilbronn, Germany).

Workup

  1. additionA 35 mL glass pressure tube (Ace Glass Cat#8648-07) containing a stir bar
  2. customan O-ring and the tubes were placed in an oil bath on a VWR
  3. temperaturemaintained at this temperature for 16 hours during which time the solution
  4. customThe tube was removed from the bath
  5. additionmixed vigorously on a vortexing mixer
  6. additionto completely mix the two layers
  7. customreplaced into the oil bath at 90° C.
  8. temperaturethe temperature raised to 100° C
  9. temperatureThe tube was heated for another hour
  10. additionmixed vigorously a second time
  11. waitfollowed by another hour
  12. temperatureof heating at 100° C
  13. extractionThe liquid was extracted with equal volumes of ethyl acetate three times
  14. customfollowed by rotary evaporation
  15. customto remove the residual ethyl acetate

Sources & evidence

ORD record
ord-c32e621cf18940e9a18bd2998589f013
Source dataset
uspto-grants-2016_06
Patent number
US09376709B2

Reaction notes

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