Allyl bromide → N,N-Dimethyl-N-(prop-2-en-1-yl)octadecan-1-aminium chloride

HRID 1388870Notes

Reaction equation

HRID 1388870 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH2:22]([Cl:25])[CH:23]=[CH2:24].C(Br)C=C.C(=O)(O)[O-].[Na+]>C(O)(C)C>[Cl-:25].[CH2:22]([N+:2]([CH3:1])([CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:23]=[CH2:24]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 7850Allyl chlorideHCID 15365DimethyloctadecylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 20468836N,N-Dimethyl-N-(prop-2-en-1-yl)octadecan-1-aminium chloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 2-liter reaction vessel equipped with a mechanical stirrer and a reflux condenser was charged with 660.0 gm. dimethyl octadecyl amine, 199.0 gm. (2.19 mol) allyl chloride, 13.3 (0.11 mol) gm. allyl bromide, 20 gm. sodium bicarbonate, and 350 ml. isopropyl alcohol. This mixture was heated under reflux overnight. Analyses of a filtered aliquot indicated the reaction was complete. The mixture was filtered and upon analysis had an Effective gram MW of 496.74.

Workup

  1. customA 2-liter reaction vessel
  2. customequipped with a mechanical stirrer and a reflux condenser
  3. additionwas charged with 660.0 gm
  4. temperatureThis mixture was heated
  5. temperatureunder reflux overnight
  6. filtrationThe mixture was filtered and upon analysis

Sources & evidence

ORD record
ord-31c201d1fc7b4a01b6dd2e904ca8cfbe
Source dataset
uspto-grants-1984_02
Patent number
US04434076

Reaction notes

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