Thionyl Chloride → N-(2-Chloroethyl)-N-ethylaniline

HRID 1053558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053558
[CH2:1]([N:3]([CH2:10][CH2:11]O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].O=S(Cl)[Cl:15]>C(Cl)Cl>[Cl:15][CH2:11][CH2:10][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 623382-(N-ethylanilino)ethanol

Produkt 1

HCID 7093N-(2-Chloroethyl)-N-ethylanilineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(N-ethyl-N-phenylamino)ethanol (10 g, 60 mmol) in CH2Cl2 (150 mL) was reacted with SOCl2 (8.8 mL, 121 mmol). The mixture was heated to reflux for one hour and quenched. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide intermediate 3a (5.54 g, 30 mmol, 50%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.28 (m, 2H), 6.74 (m, 3H), 3.65 (m, 4H), 3.46 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C10H15ClN [M+H]+: 184.0893, found: 184.0836.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. customquenched
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-10ee897f956d460b9ad1acca3f7d5308
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394233B2

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