Phosphorus tribromide → N-(2-Bromoethyl)-N,N-dimethylhexadecan-1-aminium bromide

HRID 248787Notes

Reaction equation

HRID 248787 reaction equation
[Br-:1].[CH3:2][N+:3]([CH3:23])([CH2:20][CH2:21]O)[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][CH3:19].P(Br)(Br)[Br:25]>C1C=CC=CC=1>[Br-:25].[CH3:2][N+:3]([CH3:23])([CH2:20][CH2:21][Br:1])[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][CH3:19]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 10960220Hexadecyl(2-hydroxyethyl)dimethylazanium bromide

Product 1

HCID 14625789N-(2-Bromoethyl)-N,N-dimethylhexadecan-1-aminium bromideYield 213.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A total of 3.95g (0.010 mole) of dimethyl-(2-hydroxy)ethyl-hexadecyl ammonium bromide and 0.9910g (0.00366 mol phosphorous tribromide was slurried in 20 ml of benzene and allowed to react at room temperature (about 25° C.) with stirring for 24 hours under nitrogen. The solvent was removed in vacuo and the residue washed several times with anhydrous ether. The resulting amorphous solid was recrystallized from ethyl acetate, filtered and dried to yield 3.57g (77%) of the desired product. Calc. % C 52.51, % H 9.49, %N 3.06, %Br 34.93; Found % C 51.80, H 10.06, %N 3.06, % Br 34.18; m.p. 185°-190° C. The 1H NMR and IR agree with the proposed structure.

Workup

  1. customto react at room temperature (about 25° C.)
  2. customThe solvent was removed in vacuo
  3. washthe residue washed several times with anhydrous ether
  4. customThe resulting amorphous solid was recrystallized from ethyl acetate
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-309c2167908a4d9ebd851723455230b7
Source dataset
uspto-grants-1993_05
Patent number
US05211942

Reaction notes

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