Aniline → O-Ethylacetanilide

HRID 925026

Reaktionsgleichung

Reaktionsgleichung von HRID 925026
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].CCN(CC)CC.[C:17](Cl)(=[O:19])[CH3:18].NC1C=CC=CC=1>O.ClCCl>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:17](=[O:19])[CH3:18])[CH3:2]

Komponenten

7

Edukt 4

HCID 6115AnilineHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 113572-Ethylaniline

Produkt 1

HCID 36332O-EthylacetanilideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-ethylaniline (12.4 mL, 100 mmol) and NEt3 (15.4 mL, 110 mmol) were added to 100 mL of dichloromethane and cooled to 0° C. Acetyl chloride (7.10 mL 100 mmol) was added dropwise to the cooled aniline solution, affording a peach colored suspension after complete addition. The slurry was warmed to room temperature and heated to reflux overnight. The suspension was taken to dryness and the solid was treated with 200 mL of water. The solid was collected by filtration, washed with 200 mL of diethylether and dried in vacuo, yielding 9.45 g (58%) of white solid. 1H NMR (400 MHz, CDCl3): 7.68 (d, 1H), 7.26-7.11 (m, 4H), 2.59 (q, 2H), 2.18 (s, 3H), 1.22 (t, 3H).

Aufarbeitung

  1. customaffording a peach colored suspension
  2. additionafter complete addition
  3. temperatureThe slurry was warmed to room temperature
  4. temperatureheated
  5. temperatureto reflux overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with 200 mL of diethylether
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aee044eca39b4b1f8590e87e55ace7c8
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283555B2

Verknüpfte Notizen

Wird geladen…