4-Chlorophenol → N-[2-(4-Chlorophenoxy)ethyl]-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamide

HRID 467962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467962
[OH:1][CH2:2][CH2:3][N:4]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:5]([C:7]1[N:8]=[CH:9][N:10]([CH3:12])[CH:11]=1)=[O:6].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O.O1CCCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([O:1][CH2:2][CH2:3][N:4]([CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:5]([C:7]2[N:8]=[CH:9][N:10]([CH3:12])[CH:11]=2)=[O:6])=[CH:22][CH:21]=1

Komponenten

7

Edukt 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58049384N-(2-Hydroxyethyl)-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamide

Produkt 1

HCID 46916820N-[2-(4-Chlorophenoxy)ethyl]-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamideAusbeute 47,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of N-(2-hydroxyethyl)-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamide (150 mg), p-chlorophenol (114 mg), triphenylphosphine (217 mg) and tetrahydrofuran (3.8 mL), DIAD (172 μL) was added under cooling with ice and the resulting mixture was stirred at room temperature for 3 days. To the reaction mixture, water was added and extraction was conducted with diethyl ether. The diethyl ether layer was dried over anhydrous sodium sulfate. After filtering off the desiccant, the solvents were distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=99:1 and NH silica gel cartridge; hexane/ethyl acetate=1:3 to 1:9) to give the titled compound (103 mg).

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. extractionextraction
  4. dry with materialThe diethyl ether layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtering off the desiccant
  6. distillationthe solvents were distilled off under reduced pressure
  7. customthe resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=99:1 and NH silica gel cartridge; hexane/ethyl acetate=1:3 to 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-f9f1110ad3b642ad88c744b25b372432
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623898B2

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