Acrylonitrile → 1,3-Di(n-hexadecyloxy)-2-(2-cyanoethylamino)propane

HRID 2058395

Reaktionsgleichung

Reaktionsgleichung von HRID 2058395
[CH2:1]([O:17][CH2:18][CH:19]([NH2:38])[CH2:20][O: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][CH3:16].[C:39](#[N:42])[CH:40]=[CH2:41].[OH-].[Na+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:1]([O:17][CH2:18][CH:19]([NH:38][CH2:41][CH2:40][C:39]#[N:42])[CH2:20][O: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][CH3:16]

Komponenten

5

Edukt 4

HCID 7855Acrylonitrile2×HCID 14798Sodium Hydroxide2×HCID 2723671Tetrabutylammonium HydroxideHCID 184272321,3-Dihexadecyloxy-2-aminopropane

Produkt 1

HCID 234661191,3-Di(n-hexadecyloxy)-2-(2-cyanoethylamino)propaneAusbeute 36 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1,3-di(n-hexadecyloxy)-2-aminopropane (500 mg., 0.93 mmoles), acrylonitrile (75 ml.) and 2 wt. % aqueous sodium hydroxide solution (75 ml.) was heated to 60° C. Tetrabutyl ammonium hydroxide (1 ml. of 40 wt. % aqueous solution) was then added and the resulting mixture stirred for 15 minutes at 90° C. The reaction mixture was then cooled, causing precipitation of solids, which were isolated by filtration and found (TLC) to contain a large quantity of unreacted starting material. Using fresh acrylonitrile and aqueous sodium hydroxide solution in each cycle, the solids were treated two more times by the above procedure The third cycle solid product was purified by silica gel chromatography (elution with toluene:ethyl acetate) [200 mg., 36% yield, m.p. 45°-46° C., ir (CHCl3) 2250 cm-1, n.m.r. (CDDl3) δ3.07 (t, 2, --NHCH2CH2CN) and 2.53 (t, 2, --NHCH2CH2CN)].

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. customprecipitation of solids
  3. customwhich were isolated by filtration
  4. additionthe solids were treated two more times by the above procedure The third cycle solid product
  5. customwas purified by silica gel chromatography (elution with toluene:ethyl acetate) [200 mg., 36% yield, m.p. 45°-46° C., ir (CHCl3) 2250 cm-1, n.m.r. (CDDl3) δ3.07 (t, 2, --NHCH2CH2CN) and 2.53 (t, 2, --NHCH2CH2CN)]

Quellen und Nachweise

ORD-Eintrag
ord-60161ade23584d2aa75cc0b1a31eb419
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04215146

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