Water → 1-Heptyl-2,4,5-trimethyl-1H-imidazole

HRID 1380335Notes

Reaction equation

HRID 1380335 reaction equation
Cl.[CH3:2][C:3]1[NH:4][C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=1.[H-].[Na+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>CN(C)C=O>[CH2:12]([N:4]1[C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=[C:3]1[CH3:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 6790128170807-89-5

Product 1

HCID 201883001-Heptyl-2,4,5-trimethyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 16.0 g (0.019 mole) of 2,4,5-trimethyl-1H-imidazole hydrochloride in 125 ml dry N,N-dimethylformamide and cool to 0° C. Add 8.75 g (0.218 mole) of sodium hydride (60%), stir at 0° C. for 30 minutes and then heat reaction mixture to 100° C. for one hour. Cool to 0° C. and then add 18.0 ml (0.114 mole) of n-heptyl bromide to reaction mixture. Upon completion of addition, heat to 100° C. for four hours, following the progress of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5). At the completion of the reaction, cool to room temperature and add 2 ml water. Filter precipitated salts and evaporate solvent.

Workup

  1. temperatureheat
  2. customreaction mixture to 100° C. for one hour
  3. temperatureCool to 0° C.
  4. customto reaction mixture
  5. additionUpon completion of addition
  6. temperatureheat to 100° C. for four hours
  7. customthe progress of the reaction by thin-layer chromatography on silica gel (methanol:1M sodium chloride, 95:5)
  8. customAt the completion of the reaction
  9. temperaturecool to room temperature
  10. filtrationFilter
  11. customprecipitated salts
  12. customevaporate solvent

Sources & evidence

ORD record
ord-4d6ca3d360ff473f83e417239ab4226e
Source dataset
uspto-grants-1986_04
Patent number
US04581370

Reaction notes

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