1,1-Dichloroethane → HCID 67065316, Verbindung

HRID 2403074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2403074
[CH:1]1([NH:7][C:8](=[O:28])[CH2:9][C:10]2[CH:15]=[C:14]([I:16])[C:13]([O:17][C:18]3[CH:23]=[C:22]([I:24])[C:21]([OH:25])=[C:20]([I:26])[CH:19]=3)=[C:12]([I:27])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:35][CH:36](Cl)[CH3:37]>>[Cl:35][CH2:36][CH2:37][O:25][C:21]1[C:22]([I:24])=[CH:23][C:18]([O:17][C:13]2[C:14]([I:16])=[CH:15][C:10]([CH2:9][C:8]([NH:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:28])=[CH:11][C:12]=2[I:27])=[CH:19][C:20]=1[I:26]

Komponenten

4

Edukt 3

HCID 63651,1-DichloroethaneHCID 10796Cesium carbonateHCID 67065315HCID 67065315, Verbindung

Produkt 1

HCID 67065316HCID 67065316, VerbindungAusbeute 5 %

Versuchsvorschrift

Compound 4 (2.0 g, 2.1 mmol, 1.0 eq.) was dissolved in anhydrous dichloroethane (30 mL) and then Cs2CO3 (1.7 g, 5.2 mmol, 2.5 eq.) was added. The reaction medium was then slowly heated to reflux. The mixture was stirred for 12 hrs. upon reflux then cooled to room temperature, filtered and the solvent was removed under vacuum. The residual oil then was purified by column chromatography (DCM/hexanes 80/20). The product was further recrystallized to give 2-(4-(4-(2-chloroethoxy)-3,5-diiodophenoxy)-3,5-diiodophenyl)-N-cyclohexylacetamide, compound 15, (94 mg, 0.1 mmol) as a powder.

Aufarbeitung

  1. temperatureThe reaction medium was then slowly heated to reflux
  2. temperatureupon reflux
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum
  5. customThe residual oil then was purified by column chromatography (DCM/hexanes 80/20)
  6. customThe product was further recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-5b4c2127a0ff4e568fcfd5ae9c1614c9
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802240B2

Notizen zur Reaktion

Wird geladen…