StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

N,N'-Dimethylethylenediamine → 1,2-Bis(4-aminophenyl)-1,2-ethanedione

HRID 525636
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525636
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(=O)(OC(C)(C)C)[NH2:10].Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]([C:28]2[CH:33]=CC(Br)=[CH:30][CH:29]=2)=[O:27])=[O:25])=[CH:20][CH:19]=1.CN[CH2:37][CH2:38][NH:39]C>[Cu]I.C1COCC1>[NH2:10][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]([C:28]2[CH:33]=[CH:37][C:38]([NH2:39])=[CH:30][CH:29]=2)=[O:27])=[O:25])=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 964304,4'-Dibromobenzil

Produkt 1

HCID 2751371,2-Bis(4-aminophenyl)-1,2-ethanedione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A Schlenk flask was thoroughly flame-dried under vacuum and then under nitrogen atmosphere (three cycles each). To this was added copper (I) iodide (4.14 g, 22 mmol), tribasic potassium phosphate (46.2 g, 220 mmol), and t-butyl carbamate (13.92 g, 119 mmol). These reagents were dried under vacuum and back-filled with nitrogen (three cycles). To this was added 4,4′-dibromobenzil, 1 (20 g, 54 mmol), N,N′-dimethylethylenediamine (3.82 g (4.7 mL), 43 mmol) and anhydrous THF (100 mL). The reaction flask was sealed under nitrogen and heated at 90° C. for 24 h. After bringing down to room temperature, the reaction mixture was passed through silica gel to remove the copper salts. The product was extracted with ethyl acetate and purified by column chromatography using 1:4 mixtures of ethyl acetate and hexane as eluant to obtain yellow crystalline solid. Yield: 17.5 g (73%). Mp. 207° C. 1H NMR (acetone-d6, 400 MHz): 1.50 (s, 18H), 7.78 (m, 4H), 7.89 (m, 4H), 8.98 (bs, 2H). 13C NMR (acetone-d6, 100 MHz): 194.5, 153.2, 146.9, 131.3, 128.0, 118.5, 81.1, 28.4. FT-IR (cm−1): ν 3332, 2925, 1682, 1598, 1509, 1455, 1414, 1368, 1313, 1221, 1169, 1144, 1050, 996, 914, 885, 830, 771. HRMS-FAB: mlz M+ calcd 440.1947. found 440.1938.

Aufarbeitung

  1. customA Schlenk flask was thoroughly flame-dried under vacuum
  2. customThese reagents were dried under vacuum
  3. additionback-filled with nitrogen (three cycles)
  4. customThe reaction flask was sealed under nitrogen
  5. customAfter bringing down to room temperature
  6. customto remove the copper salts
  7. extractionThe product was extracted with ethyl acetate
  8. custompurified by column chromatography
  9. customto obtain yellow crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-b394aab82d984e79a8b206648bf8d316
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340635B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion