Trimethylamine → Benzenemethanaminium, N,N-dimethyl-N-2-propenyl-, chloride

HRID 1413072Notes

Reaction equation

HRID 1413072 reaction equation
C([CH:3]([Cl:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=C.[CH3:11][C:12]([CH3:14])=O.C(C(CC)=O)C.[CH3:21][N:22](C)[CH3:23]>O>[Cl-:10].[CH:12]([CH2:14][N+:22]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)([CH3:23])[CH3:21])=[CH2:11]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 86736269HCID 86736269, compound

Product 1

HCID 11287299Benzenemethanaminium, N,N-dimethyl-N-2-propenyl-, chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
26 °C

Procedure

477 grams (3.05 mole) of 98% vinylbenzyl chloride is dissolved in 2070 ml. of acetone:diethylketone (1:1 vol). While maintaining a batch temperature of 19°-24° C., 200 grams of trimethylamine is added to this solution over a period of six hours by bubbling the gaseous amine into the stirred, cooled solution. After stirring the resulting batch at ambient temperature (26° C.) for one hour, 1300 ml. of solvent is removed under vacuum. (This solvent mixture is saved and reused in subsequent preparations.) The resulting hydroscopic solid is dried in the reaction flask at reduced pressure and ambient temperature. 634 grams (90% yield) of resulting solid product is then carefully transferred to a tightly sealed bottle for storage to prevent water pickup.

Workup

  1. additionis added to this solution over a period of six hours
  2. customby bubbling the gaseous amine into the stirred
  3. temperaturecooled solution
  4. customof solvent is removed under vacuum
  5. custom) The resulting hydroscopic solid is dried in the reaction flask at reduced pressure and ambient temperature
  6. custom634 grams (90% yield) of resulting solid product

Sources & evidence

ORD record
ord-b58fa7e5e65744acad6d5b93953a6947
Source dataset
uspto-grants-1981_02
Patent number
US04248797

Reaction notes

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