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

HRID 1053585Notes

Reaction equation

HRID 1053585 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 15a (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.

Workup

  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

Sources & evidence

ORD record
ord-f9d62a1b57d74f5fbc56bf9fb1869481
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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