Acetyl chloride → N-[2-(Acetyloxy)ethyl]-N,N-dimethyldodecan-1-aminium bromide

HRID 728384Notes

Reaction equation

HRID 728384 reaction equation
[Br-:1].[CH2:2]([N+:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][OH:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(=O)([O-])[O-].[Na+].[Na+].[C:26](Cl)(=[O:28])[CH3:27]>CC(C)=O>[Br-:1].[CH2:2]([N+:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][O:17][C:26](=[O:28])[CH3:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 814861-Dodecanaminium, N-(2-hydroxyethyl)-N,N-dimethyl-, bromide (1:1)

Product 1

HCID 13914766N-[2-(Acetyloxy)ethyl]-N,N-dimethyldodecan-1-aminium bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

In a reaction vessel was placed 13.14 grams of dodecyldimethyl 2-hydroxyethylammonium bromide, 21.22 grams of acetone solvent and 4.72 grams of sodium carbonate. While stirring under nitrogen, 3.27 grams of acetyl chloride was added dropwise. Gas evolution occurred. The mixture was then refluxed (ca. 60° C.) for 6 hours. The solvent was removed under vacuum. The residue was extracted with isopropanol to dissolve the quat and the solution was filtered hot to remove sodium chloride and sodium carbonate. The filtrate was evaporated under vacuum leaving as the product dodecyldimethyl 2-acetyloxyethylammonium bromide.

Workup

  1. customIn a reaction vessel was placed
  2. customThe solvent was removed under vacuum
  3. extractionThe residue was extracted with isopropanol
  4. dissolutionto dissolve the quat
  5. filtrationthe solution was filtered hot
  6. customto remove sodium chloride and sodium carbonate
  7. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-16b4965764b544e68863fdbaee2311b6
Source dataset
uspto-grants-1991_09
Patent number
US05047577

Reaction notes

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