1-Phenethylimidazole → HCID 86734179, compound

HRID 1730220Notes

Reaction equation

HRID 1730220 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][S:15]([O:18][CH2:19][CH:20]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[Cl:38])[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])(=[O:17])=[O:16]>CN(C)C=O>[CH3:14][S:15]([O-:18])(=[O:17])=[O:16].[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[CH:20]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[Cl:38])[CH2:19][N+:11]1[CH:12]=[CH:13][N:9]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 102196211-PhenethylimidazoleHCID 21443040HCID 21443040, compound

Product 1

HCID 86734179HCID 86734179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.6 parts of 1-(2-phenylethyl)-1H-imidazole, 24.5 parts of 2,4-dichloro-β-(2,4-dichlorophenylmethoxy)benzeneethanol methanesulfonate and 150 parts of N,N-dimethylformamide is stirred and refluxed overnight. The mixture is allowed to cool to room temperature, poured onto water and extracted twice with trichloromethane. The combined organic phases are washed three times with water, dried, filtered and evaporated, yielding 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium methanesulfonate as an oily residue. The oily residue is taken up in ethanol and brought on an ion exchange column (Amberlite IRA 400) previously converted into the hydroxyl form by treatment with a sodium hydroxide solution. The product in the form of a quaternary imidazolium hydroxide is eluted with ethanol and to the eluate there are added 30 parts of a concentrated hydrochloric acid solution. After evaporating off the solvent there is obtained 1-[2,4-dichloro-62 -(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium chloride, m.p. 158.9° C.

Workup

  1. temperaturerefluxed overnight
  2. additionpoured onto water
  3. extractionextracted twice with trichloromethane
  4. washThe combined organic phases are washed three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6d40b0de7d4041658791cc2a50e494a9
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Reaction notes

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