Dimethylformamide → [3-(4-{1-[4-(4-Chloro-phenoxy)-phenyl]-2-phenethyl-1h-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

HRID 17701

Reaktionsgleichung

Reaktionsgleichung von HRID 17701
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:2]=1.C[N:17]([CH:19]=O)C.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:27][CH:26]=1)=O>O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[CH:2]=[CH:1][C:6]([N:7]3[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:27][CH:26]=4)[N:17]=[C:19]3[CH2:22][CH2:23][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:5][CH:4]=2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 75784-(4-Chlorophenoxy)anilineHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

Produkt 1

HCID 59698958[3-(4-{1-[4-(4-Chloro-phenoxy)-phenyl]-2-phenethyl-1h-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-amino-4′-chlorodiphenyl ether (1.2 eq., 6.2 mmol) in anhydrous DMF (10 mL) DIEA (3 eq. 16 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (5.2 mmol), according to General Procedure R2. The reaction mixture was stirred under nitrogen at rt until completion, as indicated by TLC or HPLC. The reaction mixture was then diluted with cold H2O and the product was extracted in EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product obtained from 2-4% MeOH/DCM (yield˜22%).

Aufarbeitung

  1. extractionthe product was extracted in EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of solvent in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-28e6c96c13264bb8a1fd6caeddba1f98
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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