Benzene → 2-(Cyclohexen-1-yloxy)methyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole

HRID 1005517

Reaction equation

HRID 1005517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:23]1([O:17][CH2:16][C:13]2[N:14]([CH3:15])[C:10]([S:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)=[C:11]([CH:18]([CH3:20])[CH3:19])[N:12]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 702641-MethoxycyclohexeneHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanolHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 187919892-(Cyclohexen-1-yloxy)methyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazoleYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound 14 (166 mg, 0.5 mmol), 1-methoxycyclohexene (280 mg, 2.50 mmol) and p-toluenesulfonic acid pyridinium (132 mg, 0.505 mmol) was dissolved in toluene (4 mL). The reaction mixture was stirred at room temperature for 20 hours. Benzene (60 mL) was added thereto, the reaction mixture was heated under reflux over 45 minutes and concentrated to a small amount. A drop of triethylamine was added to the reaction mixture, and the mixture was filtered to remove the insoluble matter. The filtrate was concentrated under reduced pressure. The residue was extracted with hexane, and filtered off the insoluble matter. The filtrate was purified by chromatography on an alumina column (eluate: toluene) to give the compound 17 (61 mg, 30%) as crystals. Mp 69-71° C. Rf 0.57 (Al2O3 60, Type E, toluene).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux over 45 minutes
  3. concentrationconcentrated to a small amount
  4. additionA drop of triethylamine was added to the reaction mixture
  5. filtrationthe mixture was filtered
  6. customto remove the insoluble matter
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. extractionThe residue was extracted with hexane
  9. filtrationfiltered off the insoluble matter
  10. customThe filtrate was purified by chromatography on an alumina column (eluate: toluene)

Sources & evidence

ORD record
ord-36badcf1f3224d059e74dd51e7602ed3
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Linked notes

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