Ethyl Bromide → HCID 23331868, compound

HRID 903902Notes

Reaction equation

HRID 903902 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[O:4][CH:5]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[CH:6]([OH:11])[C:7]([CH3:10])([CH3:9])[CH3:8].[H-].[Na+].[CH2:24](Br)[CH3:25]>O1CCOCC1>[CH2:24]([O:11][CH:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[CH:5]([O:4][C:3]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:2]=1[Cl:1])[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[CH3:25]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 12766918HCID 12766918, compound

Product 1

HCID 23331868HCID 23331868, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

33 g (0.1 mol) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-1-imidazol-1-yl-butan-2-ol were dissolved in 150 ml of dioxane and the solution was added dropwise to 3.5 g of 80% strength sodium hydride in 150 ml of dioxane. The mixture was stirred for 3 hours at room temperature. After addition of 13.1 g (0.12 mol) of ethyl bromide, the mixture was stirred under reflux for further 17 hours. After cooling, the solvent was distilled off in vacuo, the residue was taken up in 600 ml of methylene chloride and the methylene chloride solution was washed twice with 1,000 ml of water each time, dried over sodium sulphate and distilled under a high vacuum. 10 g (28% of theory) of 2-ethoxy-1-(2,4-dichlorophenoxy)-3,3-dimethyl-1-imidazol-1-yl-butane of boiling point 170°-175° C./0.2 mm Hg were obtained.

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for further 17 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off in vacuo
  5. washthe methylene chloride solution was washed twice with 1,000 ml of water each time
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled under a high vacuum

Sources & evidence

ORD record
ord-45c8e31d68d44a29850e31783feaa503
Source dataset
uspto-grants-1980_10
Patent number
US04229459

Reaction notes

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