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

HRID 1005508

反応式

HRID 1005508 の反応式
[CH3:1][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]([CH3:8])[CH:7]=1.O.[C:25]1(C)[CH:30]=[CH:29][C:28](S(O)(=O)=O)=[CH:27][CH:26]=1.C1(C)C=CC=CC=1.COC1CCCCC=1>C(Cl)Cl>[C:25]1([O:19][CH2:18][CH2:17][O:16][CH2:15][N:14]2[C:10]([S:9][C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=3)=[C:11]([CH:21]([CH3:23])[CH3:22])[N:12]=[C:13]2[CH3:20])[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 702641-MethoxycyclohexeneHCID 4781802-[5-(3,5-Dimethyl-phenylsulfanyl)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]-ethanolHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 187920371-[2-(Cyclohexen-1-yloxy)ethoxymethyl]-5-(3,5-dimethylphenylthio)-4-isopropyl-2-methyl-1H-imidazole収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of the compound 1 (33.4 mg, 0.1 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 a mixture of dioxane (2 mL) - benzene (0.5 mL), to which was added 1-methoxycyclohexene (112 mg, 1.00 mmol). The reaction mixture was heated under reflux, and concentrated to a small volume over 1 hour. A drop of triethylamine was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Hexane was added to the residue, 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 same compound 6 (31 mg, 75%) as oil. Rf 0.62 (Al2O3 60, Type E, 2:1 hexane -EtOAc).

後処理

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of dioxane (2 mL) - benzene (0.5 mL), to which
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux
  5. concentrationconcentrated to a small volume over 1 hour
  6. additionA drop of triethylamine was added to the reaction mixture
  7. concentrationthe mixture was concentrated under reduced pressure
  8. additionHexane was added to the residue
  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))

出典と根拠

ORDレコード
ord-44cf4febb0354ec187e3d5f7e36ddeaa
出典データセット
uspto-grants-2000_04
特許番号
US06054591

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