Dimethylformamide → 2-butyl-4-[4-(4-ethyl-hexyloxy)-phenyl]-1-[4-(4-methoxy-naphthalen-1-yl-oxy)-phenyl]-1H-imidazole

HRID 2237039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2237039
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C[N:22]([CH:24]=O)C.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39]N(CC)CC)=[CH:32][CH:31]=1)=O>O.CCOC(C)=O>[CH2:6]([C:24]1[N:18]([C:17]2[CH:16]=[CH:15][C:14]([O:13][C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:20][CH:19]=2)[CH:27]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH:3]([CH2:12][CH3:11])[CH2:4][CH3:5])=[CH:34][CH:35]=2)[N:22]=1)[CH2:7][CH2:8][CH3:9]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 669774504-(4-Methoxy-naphthalen-1-yloxy)anilineHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

Produkt 1

HCID 669775342-butyl-4-[4-(4-ethyl-hexyloxy)-phenyl]-1-[4-(4-methoxy-naphthalen-1-yl-oxy)-phenyl]-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(4-methoxy-naphthalen-1-yloxy)aniline (1.2 eq., 2.5 mmol) in anhydrous DMF (5 mL) DIEA (3 eq. 7.5 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (2.3 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 isolated 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 used for further transformation.

Aufarbeitung

  1. washThe combined organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-ed5a8f36feb0410ab915d8f5ceb663b2
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714013B2

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