Toluene → 1-[2-(Cyclohepten-1-yloxy)ethoxymethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1H-imidazole

HRID 1005511Notes

Reaction equation

HRID 1005511 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:13]([CH3:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28](S(O)(=O)=O)=[CH:27][CH:26]=1.C1(C)C=CC=CC=1.COC1(OC)CCCCCC1>C(Cl)Cl>[C:26]1([O:19][CH2:18][CH2:17][O:16][CH2:15][N:14]2[C:10]([S:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)=[C:11]([CH:21]([CH3:23])[CH3:22])[N:12]=[C:13]2[CH3:20])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:25][CH:35]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 4781812-[5-(3,5-Dichloro-phenylsulfanyl)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]-ethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 128928771,1-Dimethoxycycloheptane

Product 1

HCID 187920321-[2-(Cyclohepten-1-yloxy)ethoxymethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1H-imidazoleYield 557.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound 8 (450 mg, 1.20 mmol) and p-toluenesulfonic acid hydrate (20.0 mg, 0.105 mmol) in a mixture of methylene chloride (1 mL) - toluene (0.1 mL) was concentrated under reduced pressure. The residue was dissolved in toluene (2 mL), to which was added 1,1-dimethoxycycloheptane (1.51 g, 12.0 mmol). The reaction mixture was heated under reflux over 1 hour and concentrated to a small quantity. A drop of triethylamine was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Hexane was added thereto, the mixture was filtered to remove the insoluble matter, and the filtrate was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1)) to give the compound 10 (275 mg, 47%) as oil. Rf 0.64 (Al2O3 60, Type E, 2:1 hexane -EtOAc).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in toluene (2 mL), to which
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux over 1 hour
  5. concentrationconcentrated to a small quantity
  6. additionA drop of triethylamine was added to the reaction mixture
  7. concentrationthe mixture was concentrated under reduced pressure
  8. additionHexane was added
  9. filtrationthe mixture was filtered
  10. customto remove the insoluble matter
  11. customthe filtrate was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1))

Sources & evidence

ORD record
ord-ec092cb8d0b741a487abef69b2e81961
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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