Benzyl Bromide → N-benzyl-N,N,N-trioctadecylammonium bromide

HRID 443176

Reaktionsgleichung

Reaktionsgleichung von HRID 443176
[CH2:1]([N:19]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[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][CH2:16][CH2:17][CH3:18].[CH2:56]([Br:63])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C1COCC1>[Br-:63].[CH2:56]([N+:19]([CH2:1][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][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 458429Trioctadecylamine

Produkt 1

HCID 85702311N-benzyl-N,N,N-trioctadecylammonium bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-benzyl-N,N,N-trioctadecylammonium bromide is prepared according to the following process. 0.10 g (0.13 mmol) trioctadecylamine, 0.30 ml (2.5 mmol) benzyl bromide (98%, Aldrich), and 3 ml THF (certified grade, Fisher) are placed into a 10 ml round-bottomed flask. The mixture is refluxed under a dry nitrogen atmosphere with stirring for 1 day. 80 mg (65%) white solid, mp 82°-83° C., is recovered after the solvent is evaporated, and the residue is recrystallized twice in a mix of hexane and ether. IR(KBr) 2916, 2851 (C-H stretching, vvs), 1473, 1386(C-H bending, w) cm-1. 1HNMR(CDCl3) δ 7.74-7.36 (aromatic H, m, 4H), 5.19-4.76 (CH2,s, 2H), 3.69-3.12(CH2, m, 6H), 2.05-0.67 (heptadecyl groups, m, 104H).

Aufarbeitung

  1. temperatureThe mixture is refluxed under a dry nitrogen atmosphere
  2. custom80 mg (65%) white solid, mp 82°-83° C., is recovered after the solvent
  3. customis evaporated
  4. customthe residue is recrystallized twice in
  5. additiona mix of hexane and ether

Quellen und Nachweise

ORD-Eintrag
ord-d5d121ce328343229c6b7b2182d51fa6
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892116

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