Stearoyl chloride → N-(2,3-Dihydroxypropyl)stearamide

Reaktionsgleichung

[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[C:7](Cl)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>N1C=CC=CC=1.CN(C=O)C>[C:7]([NH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

Versuchsvorschrift

To a mechanically stirred solution of 3-amino-1,2-propanediol (32 g, 0.35 mol) in 100 mL of pyridine and 250 mL of DMF was added a solution of stearoyl chloride (100.0 g, 0.33 mol) in 150 mL of DMF. After stirring for 1 h, precipitation occurred and an additional 100 mL of DMF was added. After 2 h, the gelatinous mass was filtered, washed with water, and air dried. The solid was recrystallized successively from EtOH, isopropanol, and chloroform to give 74 g (63%) as a white powder (mp 111.5-113.5° C.). 1H-NMR: 0.86 (t, 3H, CH3), 1.25 (broad m, 28H, (CH2)14), 1.55 (m, 2H, NHCOCH2CH2), 2.20 (t, 2H NHCOCH2), 3.4 (m, 2H, CH2NH), 3.55 (d, 2H, CH2OH). 3.75 (m, 1H, CH), 5.8 (m, 1H, NH).