4-Phenoxyphenol → HCID 14535806, Verbindung

HRID 1198159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1198159
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl.Cl[CH2:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1>CN(C)C=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:21][N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 132544-PhenoxyphenolHCID 24758Sodium hydrideHCID 136927281-(Chloromethyl)-1H-benzimidazole--hydrogen chloride (1/1)HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 14535806HCID 14535806, VerbindungAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

At room temperature (about 20° C.) and under a nitrogen blanket, 13.95 g of p-phenoxyphenol in 100 ml of anhydrous dimethylformamide is dripped into 6.75 g of 80% strength sodium hydride in 50 ml of anhydrous dimethylformamide. Upon completion of hydrogen evolution, the mixture is stirred for 4 hours at 60° C. At 10° C., 15.22 g of 1-chloromethylbenzimidazole hydrochloride is then added. The mixture is stirred for 8 hours at 120° C. After concentration under reduced pressure, the residue is taken up in ethyl acetate, and washed three times with water and three times with 5% strength aqueous sodium hydroxide solution. The combined organic phases are dried over sodium sulfate and concentrated. The residue is recrystallized from diethyl ether. There is obtained 11.8 g of 1-[(p-phenoxyphenoxy)-methyl]-benzimidazole of m.p. 112° C.

Aufarbeitung

  1. customAt room temperature
  2. custom(about 20° C.)
  3. concentrationAfter concentration under reduced pressure
  4. washwashed three times with water and three times with 5% strength aqueous sodium hydroxide solution
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-00de4275cec842a690b2c11db4e07e56
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05280036

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