Dioctadecylamine → 1-(Dioctadecylamino)methyl-4-cyanobenzene

HRID 258737Notes

Reaction equation

HRID 258737 reaction equation
[CH2:1]([NH:19][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].Br[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=1>C(Cl)(Cl)Cl>[CH2:20]([N:19]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=1)[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])[CH2:21][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]

Participants

4

Reactant 2

HCID 66989DioctadecylamineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 204329871-(Dioctadecylamino)methyl-4-cyanobenzeneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dioctadecylamine (26.0 g., 0.05 M), α-bromo-p-tolunitrile (4.9 g., 0.025 M) and chloroform (500 ml.) are stirred at room temperature for 24 hours. The precipitate of dioctadecylamine hydrobromide is filtered off and the filtrate concentrated under reduced pressure. The residue is slurried in methanol, filtered, and evaporated to give 1-(dioctadecylamino)methyl-4-cyanobenzene (15.5 g., 97.5% yield).

Workup

  1. filtrationThe precipitate of dioctadecylamine hydrobromide is filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6826c80fe9a447d7a2fe14cc7d63ee82
Source dataset
uspto-grants-1977_07
Patent number
US04034040

Reaction notes

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