Sodium hydride → HCID 14720860, Verbindung

HRID 36618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 36618
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:19][N:20]1[C:24]([Cl:25])=[C:23]([Cl:26])[N:22]=[CH:21]1>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:19][N:20]3[C:24]([Cl:25])=[C:23]([Cl:26])[N:22]=[CH:21]3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-HCID 146736064-(6-Chloro-2-pyridinyloxy)phenol

Produkt 1

HCID 14720860HCID 14720860, VerbindungAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

At room temperature (about 20° C.), 4.9 g of 4-(6-chloro-2-pyridinyloxy)-phenol in 40 ml of anhydrous dimethylformamide is dripped into 0.6 g of 100% strength sodium hydride in 20 ml of anhydrous dimethylformamide. The mixture is subsequently stirred for 30 minutes at 50° C, and then 4.2 g of 1-chloromethyl-4,5-dichloroimidazole in 20 ml of anhydrous dimethylformamide is dripped in at room temperature. This mixture is stirred for 2 hours at 60° C. and overnight at room temperature. It is then stirred into 200 ml of ice water and the solution is extracted three times with methyl tert-butyl ether. The organic phase is washed with 5% strength sodium hydroxide solution and water, and dried, and the solvent is evaporated off under reduced pressure. The crude product obtained is recrystallized from toluene. There is obtained 6.6 g of 1-[4-(6-chloro-2-pyridinyloxy)-phenoxymethyl]-4,5-dichloroimidazole: m.p.: 94°-98° C.

Aufarbeitung

  1. customAt room temperature
  2. customis dripped in at room temperature
  3. stirringThis mixture is stirred for 2 hours at 60° C. and overnight at room temperature
  4. extractionthe solution is extracted three times with methyl tert-butyl ether
  5. washThe organic phase is washed with 5% strength sodium hydroxide solution and water
  6. customdried
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe crude product obtained
  9. customis recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-d32386d5b1104b7c88d677d92e2a3a7a
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416100

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