Imidazole → (2,4-Dichlorobenzyl)-{4-[1-(1-imidazolyl)-ethyl]-phenyl}-ether

HRID 435880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 435880
CC(C1C=CC(O)=CC=1)=O.[H-].[Na+].ClC1C=C(Cl)C=CC=1CCl.[BH4-].[Na+].[Cl:25][C:26]1[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:27]=1[CH2:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([CH:34](O)[CH3:35])=[CH:32][CH:31]=1.S(Cl)(Cl)=O.[NH:48]1[CH:52]=[CH:51][N:50]=[CH:49]1.[Na].N1C=CN=C1.Cl([O-])(=O)(=O)=O>C(O)C.O1CCOCC1.C(Cl)Cl.CCOCC.CN(C)C=O>[Cl:25][C:26]1[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:27]=1[CH2:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([CH:34]([N:48]2[CH:52]=[CH:51][N:50]=[CH:49]2)[CH3:35])=[CH:32][CH:31]=1

Komponenten

13

Edukt 9

HCID 795ImidazoleHCID 72122,4-Dichlorobenzyl chlorideHCID 74694'-HydroxyacetophenoneHCID 24386Thionyl ChlorideHCID 24758Sodium hydride2×HCID 123351PerchlorateHCID 27638091-{4-[(2,4-Dichlorobenzyl)oxy]phenyl}-1-ethanolHCID 4311764Sodium borohydrideHCID 57373095Imidazole sodium

Produkt 1

HCID 21481630(2,4-Dichlorobenzyl)-{4-[1-(1-imidazolyl)-ethyl]-phenyl}-ether

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 21881112Ethyl ether methylene chlorideLösungsmittelHCID 22560076Dioxan ethanolLösungsmittel

Versuchsvorschrift

136 g. of 4-hydroxyacetophenone is etherified in 500 ml. of dimethylformamide with 30 g. of sodium hydride oil suspension (80%) and 195 g. of 2,4-dichlorobenzyl chloride analogously to Example 16. The thus-obtained 4-(2,4-dichlorobenzyloxy)-acetophenone (290 g., m.p. 89°-90° ) is reduced in 1 liter of ethanol/dioxane (2 : 1) with 50 g. of sodium borohydride analogously to Example 26, and worked up. Of the thusobtained 4-(2,4-dichlorobenzyloxy)-α-methylbenzyl alcohol (m.p. 61°-64°), 1.7 g. is stirred with 5 ml. of thionyl chloride for 1 hour at room temperature. The product remaining after a careful evaporation of the thionyl chloride is reacted according to Example 15 with a solution of sodium imidazole, prepared from 360 mg. of imidazole and 160 mg. of sodium hydride, and converted into the perchlorate as described in Example 26. Yield: 940 mg.; m.p. 103°-106° (methylene chloride/ether).

Aufarbeitung

  1. customafter a careful evaporation of the thionyl chloride
  2. customis reacted
  3. customprepared from 360 mg

Quellen und Nachweise

ORD-Eintrag
ord-5ed9b102d1c64c41af75af68dcd5ccb6
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04006243

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