Water → 1-[4-(4-Chlorophenyl)-2-(4-acetylaminobenzyloxy)-n-butyl]imidazole

HRID 463288

Reaktionsgleichung

Reaktionsgleichung von HRID 463288
[OH:1][CH:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[H-].[Na+].[C:20]([NH:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].O>O1CCCC1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][CH:2]([O:1][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:20](=[O:22])[CH3:21])=[CH:31][CH:30]=2)[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 148705Acetamide, N-(4-(chloromethyl)phenyl)-HCID 109559944-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

Produkt 1

HCID 202822111-[4-(4-Chlorophenyl)-2-(4-acetylaminobenzyloxy)-n-butyl]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 1.25 g of 1-[2-hydroxy-4-(4-chlorophenyl)-n-butyl]imidazole and 0.26 g of sodium hydride (50% dispersion in mineral oil) in 20 ml of tetrahydrofuran was stirred under nitrogen at room temperature for one hour, and at 60° C. for one hour. The mixture was then cooled to 0° C. and treated dropwise with stirring with 4-acetylaminobenzyl chloride in 10 ml tetrahydrofuran, keeping the temperature below 10° C. After stirring for one hour, the mixture was heated to 60° C. for 2 hours and poured into water. The product was extracted with ethyl acetate and the extracts dried (MgSO4) and evaporated. The residue was chromatographed on silica gel eluting with 2% water in ethyl acetate to give 1-[4-(4-chlorophenyl)-2-(4-acetylaminobenzyloxy)-n-butyl]imidazole.

Aufarbeitung

  1. waitat 60° C. for one hour
  2. temperatureThe mixture was then cooled to 0° C.
  3. additiontreated dropwise
  4. customthe temperature below 10° C
  5. stirringAfter stirring for one hour
  6. temperaturethe mixture was heated to 60° C. for 2 hours
  7. extractionThe product was extracted with ethyl acetate
  8. dry with materialthe extracts dried (MgSO4)
  9. customevaporated
  10. customThe residue was chromatographed on silica gel eluting with 2% water in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ef453c11282c41909ab6a884e6528924
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518607

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