Ethanolamine → 3-(2-Hydroxyethylamino)-1-tetradecylthio-2-propanol

HRID 1117Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]([S:19][CH2:20][CH:21]1[O:23][CH2:22]1)[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]>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:22][CH:21]([OH:23])[CH2:20][S:19][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]

Participants

Conditions

Temperature: 80 °C

Procedure

A 300-ml flask equipped with a stirrer and dropping funnel was charged with 61.1 g (1 mol) of ethanolamine and 61 g of ethanol. While stirring the contents at 80° C., a solution of 14.3 g (50 mmol) of 1-tetradecylthio-2,3-epoxypropane in 30 g ethanol was added dropwise over 3 hours. After completion of the dropping, the resultant reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from hexane, thereby obtaining 15.8 g (yield: 91%) of the title compound (IIe-1).

Workup

customA 300-ml flask equipped with a stirrer
customAfter completion of the dropping, the resultant reaction mixture
concentrationwas concentrated under reduced pressure
customthe residue was recrystallized from hexane

Sources & evidence

ORD record: ord-050e689426f84409ae62ef62ee510e60
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Reaction notes

Loading…