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

HRID 1194577Notes

Reaction equation

HRID 1194577 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 chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Moreover, the obtained (S)-2,3-dihydroxypropyltrimethylammonium chloride was suspended in 100 ml of dimethylformamide and then 22.57 g of thionyl chloride was added thereto at a tempareture from 5° to 10° C. After stirring for 20 minutes, it was heated for 5 hours at 100° C. Finally, after the reaction was completed and the reaction mixture was cooled to room temperature, it was evaporated to dryness and then the residue was washed with methylene chloride to give 30.20 g of (S)-3-chloro-2-hydroxypropyltrimethylammonium chloride.

Workup

  1. customfrom 5° to 10° C
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customit was evaporated to dryness
  4. washthe residue was washed with methylene chloride

Sources & evidence

ORD record
ord-501095971757421a9354fc5a6bdb2e74
Source dataset
uspto-grants-1989_03
Patent number
US04814506

Reaction notes

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