Imidazole → 1-[2-Cyclopentyl-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole

HRID 1730175Notes

Reaction equation

HRID 1730175 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CS(O[CH2:11][CH:12]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])(=O)=O>CN(C)C=O>[CH:21]1([CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH2:11][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 21499487HCID 21499487, compound

Product 1

HCID 203061511-[2-Cyclopentyl-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18 parts of 1H-imidazole, 18 parts of 2,4-dichloro-β-cyclopentylbenzeneethanol methanesulfonate and 225 parts of N,N-dimethylformamide is stirred and refluxed overnight. The reaction mixture is cooled and poured onto water. The product is extracted three times with trichloromethane. The combined extracts are washed three times with water and stirred with silicagel. The latter is filtered off and the filtrate is evaporated. The residue is crystallized from petroleumether. The product is filtered off and recrystallized from a mixture of 2,2'-oxybispropane and petroleum-ether, yielding 6.8 parts of 1-[2-cyclopentyl-2-(2,4-dichlorophenyl)-ethyl]-1H-imidazole; mp. 97.6° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted three times with trichloromethane
  5. washThe combined extracts are washed three times with water
  6. stirringstirred with silicagel
  7. filtrationThe latter is filtered off
  8. customthe filtrate is evaporated
  9. customThe residue is crystallized from petroleumether
  10. filtrationThe product is filtered off
  11. customrecrystallized from a mixture of 2,2'-oxybispropane and petroleum-ether

Sources & evidence

ORD record
ord-539c703635874fc9a98017db3bd4c3ab
Source dataset
uspto-grants-1976_11
Patent number
US03991201

Reaction notes

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