Thionyl Chloride → (3-Chloro-2-hydroxypropyl)trimethylammonium chloride

HRID 1194573

Reaction equation

HRID 1194573 reaction equation
[Cl-:1].[OH:2][CH:3]([CH2:9]O)[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].S(Cl)([Cl:13])=O>CN(C)C=O>[Cl-:13].[Cl:1][CH2:9][CH:3]([OH:2])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 161796(2,3-Dihydroxypropyl)trimethylammonium chloride

Product 1

HCID 18732(3-Chloro-2-hydroxypropyl)trimethylammonium chlorideYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

There was suspended 9.20 g of 2,3-dihydroxypropyltrimethylammonium chloride (chemical purity: 100%) in 50 ml of dimethylformamide, and thereto 6.80 g of thionyl chloride was added at a temperature from 5° to 10° C. After stirring for 20 minutes, it was heated at 100° C. for 5 hours. Finally, after cooling the reaction mixture to room temperature, 9.85 g of 3-chloro-2-hydroxypropyltrimethylammonium chloride was obtained by evaporating the reaction mixture to dryness.

Workup

  1. temperatureFinally, after cooling the reaction mixture to room temperature

Sources & evidence

ORD record
ord-238c38f59d2e443fb190bf3a294c551d
Source dataset
uspto-grants-1989_03
Patent number
US04814506

Linked notes

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