1-Methylimidazole → HCID 70387077, compound

HRID 64657Notes

Reaction equation

HRID 64657 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([Br:11])[CH3:10])=[CH:4][CH:3]=1.[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>C(OCC)C>[Br-:11].[CH3:13][NH+:14]1[CH:18]=[CH:17][N:16]([CH:9]([CH3:10])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:12])[CH2:15]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 27340632-Bromo-1-(4-methylphenyl)propan-1-one

Product 1

HCID 70387077HCID 70387077, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution 2.24 g (0.01 mol) of 1-(4-methylphenyl)-1-oxo-2-bromopropane and 0.9 g (0.011 mol) of 1-methylimidazole in 50 ml of diethyl ether was stirred at room for approximately 18 hours. The reaction solvent was decanted, and the residue was washed with diethyl ether and dissolved in acetonitrile. The resulting solution was diluted with diethyl ether and the precipitated solid was collected by filtration. The solid was recrystallized from acetonitrile/diethyl ether to afford 0.33 g of 1-methyl-3-[1-methyl-2-(4-methylphenyl)-2-oxoethyl]-1H-imidazolium bromide as a solid. (11% yield) mp=175°-177° C.

Workup

  1. customThe reaction solvent was decanted
  2. washthe residue was washed with diethyl ether
  3. dissolutiondissolved in acetonitrile
  4. additionThe resulting solution was diluted with diethyl ether
  5. filtrationthe precipitated solid was collected by filtration
  6. customThe solid was recrystallized from acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-213ef1a85db34e63bce76ce26da5f8f3
Source dataset
uspto-grants-1986_09
Patent number
US04609670

Reaction notes

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