Thionyl Chloride → HCID 86747026, compound

HRID 636325Notes

Reaction equation

HRID 636325 reaction equation
S(Cl)([Cl:3])=O.[ClH:5].[I-:6].O[CH2:8][CH2:9][N:10]([CH2:18][CH3:19])[CH2:11][CH2:12][CH2:13][N+:14]([CH3:17])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[ClH:3].[I-:6].[Cl:5][CH2:8][CH2:9][N:10]([CH2:18][CH3:19])[CH2:11][CH2:12][CH2:13][N+:14]([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86747027HCID 86747027, compound

Product 1

HCID 86747026HCID 86747026, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A total of 28 ml of thionyl chloride was added dropwise, with stirring, to 27.35 g of 3-[(2-hydroxyethyl)ethylamino]-N,N,N-trimethyl-1-propanaminium iodide hydrochloride in 200 ml of toluene at 50° C. Upon completion of the addition the mixture was stirred at 50° for 15 minutes, and then heated at 80° C. for 3 hours. The reaction mixture was steam distilled to remove toluene. Organic chloride analysis on the resulting aqueous solution showed the corresponding alkyl chloride was obtained in 88% yield.

Workup

  1. additionUpon completion of the addition the mixture
  2. distillationdistilled
  3. customto remove toluene
  4. customwas obtained in 88% yield

Sources & evidence

ORD record
ord-ef71ce8aeb2e4b3695dd9c0378a3be1c
Source dataset
uspto-grants-2001_02
Patent number
US06193843B1

Reaction notes

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