Trimethylamine → (3-Hexadecylsulfanyl-2-methoxy-propyl)-trimethyl-ammonium

HRID 977290Notes

Reaction equation

HRID 977290 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([O:22][CH3:23])[CH2:20][Br:21])[CH2:2][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][CH3:16].[CH3:24][N:25]([CH3:27])[CH3:26]>CC#N>[Br-:21].[CH2:1]([S:17][CH2:18][CH:19]([O:22][CH3:23])[CH2:20][N+:25]([CH3:27])([CH3:26])[CH3:24])[CH2:2][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][CH3:16]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 14522781(+)-1-Hexadecylthio-2-methoxy-3-bromopropane

Product 1

HCID 467804(3-Hexadecylsulfanyl-2-methoxy-propyl)-trimethyl-ammoniumYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 100 milliliter heavy wall glass tube equipped with a magnetic stir bar, was added a solution of 2.0 grams (0.005 mole) of (±)-1-hexadecylthio-2-methoxy-3-bromopropane dissolved in 50 milliliters of CH3CN and the vessel was cooled to -10° Centigrade. An excess of condensed trimethylamine was added, the tube was sealed, and the vessel was heated to 60° Centigrade for 24 hours. The reaction mixture was then cooled to room temperature, resulting in a precipitate which was filtered. The precipitate was swirled with five 50 milliliter portions of ether, the ether decanted off, and dried under vacuum, resulting in 2.1 grams (92%) of pure product, (mp 197°-199° Centigrade). 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 28H, (CH2)14 ], 2.45-3.0(m, 4H, CH2S--CH2), 3.48[s, 12H, CH3 --O, N(CH3)3 ], 3.5-4.0(m, 3H, CH--CH2N). Anal. (C23H50NOSBr) C,H,N.

Workup

  1. customTo a 100 milliliter heavy wall glass tube equipped with a magnetic stir bar
  2. temperaturethe vessel was cooled to -10° Centigrade
  3. additionwas added
  4. customthe tube was sealed
  5. temperaturethe vessel was heated to 60° Centigrade for 24 hours
  6. customresulting in a precipitate which
  7. filtrationwas filtered
  8. customthe ether decanted off
  9. customdried under vacuum

Sources & evidence

ORD record
ord-27899350ecfd443c9d48462c9a5e088e
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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