Ethanol → Benzenamine, N,N-diethyl-2-methyl-

HRID 16132

Reaktionsgleichung

Reaktionsgleichung von HRID 16132
C([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])C.[CH2:10](O)[CH3:11].[C:13](=O)([O-])[O-].[Na+].[Na+].[CH2:19](I)[CH3:20]>O>[CH2:19]([N:6]([CH2:10][CH3:11])[C:5]1[CH:4]=[CH:3][CH:9]=[CH:8][C:7]=1[CH3:13])[CH3:20]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 114753-Ethylaniline

Produkt 1

HCID 69075Benzenamine, N,N-diethyl-2-methyl-Ausbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a 100 cm3 round bottom flask was added 3-ethylaniline (5.0 g, 41.3 mmol), ethanol (7.5 cm3), sodium carbonate (5.9 g, 55.7 mmol). Ethyl iodide (17.38 g, 111.4 mmol) was added dropwise. The mixture was then heated at 45° C. for 12 hours before cooling to room temperature and adding water (50 cm3). The mixture was extracted into diethyl ether (3×50 cm3) the extracts were dried over magnesium sulphate, filtered, and concentrated to give the title compound (7.03 g, 96%) as a light yellow oil. dH (250 MHz; CDCl3): 7.20 (1H, dd, 9, 7.25, ArH), 6.60 (3H, m, ArH), 3.43 (4H, q, 7, NCH2), 2.69 (2H, q, 7.25, CH2), 1.32 (3H, t, 7.5, CH3), 1.23 (6H, t, 7, CH3); dC (62.9 MHz; CDCl3): 12.7 (CH3), 15.8 (CH3), 29.5 (CH2), 44.4 (NCH3), 109.4 (ArC), 111.4 (ArC), 115.1 (ArC), 129.2 (ArC), 145.4 (ArC), 147.9 (ArC).

Aufarbeitung

  1. temperaturebefore cooling to room temperature
  2. extractionThe mixture was extracted into diethyl ether (3×50 cm3) the extracts
  3. dry with materialwere dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-97afda8d7e3542d182acdb7a6f19eb20
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737138B2

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