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

HRID 344721Notes

Reaction equation

HRID 344721 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

5

Reactant 3

HCID 5238Sodium IodideHCID 8113DiethanolamineHCID 2696063-Chloropropyl phenyl sulfide

Product 1

HCID 543093351-Bis(hydroxyethyl)amino-3-phenylthiopropaneYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionan aqueous saturated sodium bicarbonate solution was added to the mixture
  5. extractionfollowed by extraction of the solution with chloroform 5 times
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol =25/1)

Sources & evidence

ORD record
ord-a2e5d23f57bd405797d234b4f28b2055
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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