Thionyl Chloride → N-(2-chloroethyl)-N-methyl-octadecyl ammonium chloride

HRID 1525804Notes

Reaction equation

HRID 1525804 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:9]>ClCCCl>[Cl-:3].[Cl:3][CH2:6][CH2:7][NH+:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13564486N-(2-hydroxyethyl)-N-methyl-octadecylamine

Product 1

HCID 86722748N-(2-chloroethyl)-N-methyl-octadecyl ammonium chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (0.45 mL) was dissolved in 1,2-dichloroethane (3.0 mL). The solution of N-(2-hydroxyethyl)-N-methyl-octadecylamine (1.0 g) in 1,2-dichloroethane (7.0 mL) was added thereto at 0° C., followed by stirring at 50° C. for 30 minutes. The reaction solution was concentrated under reduced pressure and azeotrope was carried out with toluene twice to obtain the title compound (1.2 g) having the following physical property values.

Workup

  1. customat 0° C.
  2. concentrationThe reaction solution was concentrated under reduced pressure and azeotrope

Sources & evidence

ORD record
ord-ea442a2ce6364d72b993fe7baaff4c19
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

Loading…