Sodium Iodide → 1-Bis(hydroxyethyl)amino-3-phenylthiopropane

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14][OH:15].[I-].[Na+]>O1CCOCC1>[OH:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][OH:18])[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Procedure

A mixture of 8.30 g (44.5 mmols) of 1-chloro-3-phenylthiopropane, 100 ml of diethanolamine, 13.3 g (88.7 mmols) of sodium iodide and 250 ml of dioxan was heated under reflux for 15 hours. The mixture was concentrated under reduced pressure, and an aqueous saturated sodium bicarbonate solution was added to the mixture followed by extraction of the solution with chloroform 5 times. The chloroform layer was drided over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol =25/1) to afford 6.46 g (yield: 57%) of 1-bis(hydroxyethyl)amino-3-phenylthiopropane.