Ethanolamine → 2-(Bis(2-hydroxyethyl)amino)ethanesulphonic acid

HRID 128207

Reaction equation

HRID 128207 reaction equation
Br[CH:2]([S:4]([O-:7])(=[O:6])=[O:5])[CH3:3].[Na+].[CH2:9]([CH2:11][NH2:12])[OH:10].[CH2:13]([OH:15])[CH3:14]>O>[OH:10][CH2:9][CH2:11][N:12]([CH2:14][CH2:13][OH:15])[CH2:3][CH2:2][S:4]([OH:7])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 702EthanolHCID 23705444Sodium bromoethanesulfonate

Product 1

HCID 732432-(Bis(2-hydroxyethyl)amino)ethanesulphonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 90 g of sodium bromoethanesulphonate (Organic Synthesis, Coll. Vol. II, p; 558) and 110 g of ethanolamine in 1500 ml of water was heated over a steam bath for about 2 hours and the reaction mixture left to stand for one night. The excess diethanolamine and water were then distilled off under vacuum, and the residue taken up in 100 ml of water and 800 ml of concentrated hydrochloric acid. The solution was cooled and filtered from the sodium chloride by a filter pump. It was then concentrated under vacuum until an oil was obtained which was taken up in boiling ethanol. On cooling, a crystalline product was obtained having a melting point of 163°-165° C., which was recrystallised from ethanol and water. 16 G of product were obtained, the analytical and spectroscopic data of which confirmed the identity of the product as the compound (III).

Workup

  1. waitthe reaction mixture left
  2. waitto stand for one night
  3. distillationThe excess diethanolamine and water were then distilled off under vacuum
  4. temperatureThe solution was cooled
  5. filtrationfiltered from the sodium chloride by a filter pump
  6. concentrationIt was then concentrated under vacuum until an oil
  7. customwas obtained which
  8. temperatureOn cooling
  9. customa crystalline product was obtained
  10. customwas recrystallised from ethanol and water
  11. custom16 G of product were obtained

Sources & evidence

ORD record
ord-d1c4e63bcd184144bf099f58d9a8b652
Source dataset
uspto-grants-1981_03
Patent number
US04259332

Linked notes

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