2-[(2-Cyclohexylphenoxy)methyl]oxirane → 1-{4-[3-(o-Cyclohexylphenoxy)-2-hydroxypropylamino]-phenyl}-2-imidazolidinone

HRID 979899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 979899
[CH:1]1([C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[O:9][CH2:10][CH:11]2[CH2:13][O:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])=[CH:21][CH:20]=1>C(O)(C)C>[CH:1]1([C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[O:9][CH2:10][CH:11]([OH:12])[CH2:13][NH:18][C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:29][CH2:28][NH:27][C:26]3=[O:30])=[CH:23][CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 124166932-[(2-Cyclohexylphenoxy)methyl]oxiraneHCID 137554911-(4-Aminophenyl)imidazolidin-2-one

Produkt 1

HCID 202230781-{4-[3-(o-Cyclohexylphenoxy)-2-hydroxypropylamino]-phenyl}-2-imidazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 3.24 g o-(cyclohexyl)-phenoxymethyloxirane (see Example 3) and 2.65 g of 1-(4-aminophenyl)-2-imidazolidinone in 60 ml isopropanol is stirred at reflux for 18 hours. The reaction mixture is filtered and the filtrate concentrated in vacuo. The residue is dissolved in 50 ml ethyl acetate and acidified to pH=1 with a solution of hydrogen chloride gas in ethyl acetate. The supernatant is decanted from the dark gum that forms and the residue is treated with ethyl acetate and 5% aqueous sodium carbonate. The ethyl acetate solution is separated, washed with 10% aqueous sodium carbonate and twice with water. After drying over anhydrous sodium sulfate the solution is treated with charcoal, filtered and concentrated in vacuo leaving a dark viscous gum. The gum is chromatographed by passing through a column of silica gel using methylene chloride/methyl alcohol as eluent to yield 1-{4-[3-(o-cyclohexylphenoxy)-2-hydroxypropylamino]-phenyl}-2-imidazolidinone, which is used directly in the next step.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThe residue is dissolved in 50 ml ethyl acetate
  5. customThe supernatant is decanted from the dark gum that
  6. additionthe residue is treated with ethyl acetate and 5% aqueous sodium carbonate
  7. customThe ethyl acetate solution is separated
  8. washwashed with 10% aqueous sodium carbonate and twice with water
  9. dry with materialAfter drying over anhydrous sodium sulfate the solution
  10. additionis treated with charcoal
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customleaving a dark viscous gum
  14. customThe gum is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-81a8ed81ebd545dba27c7ad346b0b734
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04634713

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