Trimethylamine → Oxiranemethanaminium, N,N,N-trimethyl-, bromide

HRID 2308594Notes

Reaction equation

HRID 2308594 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].[CH2:5]([CH:7]1[O:9][CH2:8]1)[Br:6]>CC(C)=O>[Br-:6].[O:9]1[CH2:8][CH:7]1[CH2:5][N+:2]([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 18430Epibromohydrin

Product 1

HCID 22046211Oxiranemethanaminium, N,N,N-trimethyl-, bromideYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

A flask equipped with a sparger, mechanical stirrer, thermometer and efficiency condenser was charged with acetone (500 milliliters) at ambient temperature. Trimethylamine (58 grams, 0.98 mol) was charged into the solution. The pot was cooled to 10° C. and epibromohydrin (137 grams, 1.0 mol) was added dropwise over a 1 hour period. The resultant cloudy solution was allowed to slowly rise to ambient temperature and stand for 60 hours. Precipitate was collected by filtration washed with acetone (60 milliliters) and dried yielding a colorless crystalline product (179.4 grams, 94%).

Workup

  1. customA flask equipped with a sparger, mechanical stirrer, thermometer and efficiency condenser
  2. customto slowly rise to ambient temperature
  3. filtrationPrecipitate was collected by filtration
  4. washwashed with acetone (60 milliliters)
  5. customdried

Sources & evidence

ORD record
ord-f0669db7f32144629ea317ebda471cdc
Source dataset
uspto-grants-1987_09
Patent number
US04690817

Reaction notes

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