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

HRID 1194575Notes

Reaction equation

HRID 1194575 reaction equation
[Cl-:1].[OH:2][C@H: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][C@@H:3]([OH:2])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13668848(S)-2,3-Dihydroxy-N,N,N-trimethylpropan-1-aminium chloride

Product 1

HCID 2793814(S)-(-)-(3-Chloro-2-hydroxypropyl)trimethylammonium chlorideYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

There was suspended 10.73 g of the obtained (S)-2,3-dihydroxypropyltrimethylammonium chloride in 50 ml of dimethylformamide, and then 7.66 g of thionyl chloride was added thereto at a temperature from 5° to 10° C. After stirring for 20 minutes, it was heated for 5 hours at 100° C. After cooling the reaction mixture to room temperature, the reaction mixture was evaporated to dryness to give 10.56 g of (S)-3-chloro-2-hydroxypropyltrimethylammonium chloride.

Workup

  1. customfrom 5° to 10° C
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. customthe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-3a13b6f681504a1abfc56d666c545c97
Source dataset
uspto-grants-1989_03
Patent number
US04814506

Reaction notes

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