Ethanolamine → N-(2-Hydroxyethylamino)-ethanesulfonic acid

HRID 128206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 128206
Br[CH:2]([S:4]([O-:7])(=[O:6])=[O:5])[CH3:3].[Na+].[CH2:9]([CH2:11][NH2:12])[OH:10]>O.C(O)C>[OH:10][CH2:9][CH2:11][NH:12][CH2:3][CH2:2][S:4]([OH:7])(=[O:6])=[O:5]

Komponenten

5

Edukt 2

HCID 700EthanolamineHCID 23705444Sodium bromoethanesulfonate

Produkt 1

HCID 12260054N-(2-Hydroxyethylamino)-ethanesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution in 2 liters of water of 315 g of sodium bromoethanesulphonate (Organic Synthesis, Coll. Vol. II, p. 558) and 450 g of ethanolamine was heated to 60°-70° C. for 30 minutes. Excess ethanolamine and water were then distilled off under vacuum, and the residue dissolved in 250-270 ml of water. 2.2 Liters of concentrated hydrochloric acid was added and the solution kept in a refrigerator for 15-20 hours. The precipitated sodium chloride was filtered off using a filter pump, and the solution concentrated until a viscous oil was obtained. The oil was diluted with 60 ml of water and ethanol (about 500 ml) then added to precipitate the reaction product. After the mixture has been left one night in a refrigerator, precipitation was almost complete. The product obtained was filtered off with a filter pump. About 130-140 g of crystalline product was obtained, having a melting point of 180°-183° C.

Aufarbeitung

  1. distillationExcess ethanolamine and water were then distilled off under vacuum
  2. dissolutionthe residue dissolved in 250-270 ml of water
  3. addition2.2 Liters of concentrated hydrochloric acid was added
  4. filtrationThe precipitated sodium chloride was filtered off
  5. concentrationthe solution concentrated until a viscous oil
  6. customwas obtained
  7. additionthen added
  8. customto precipitate the reaction product
  9. waitAfter the mixture has been left one night in a refrigerator, precipitation
  10. customThe product obtained
  11. filtrationwas filtered off with a filter pump

Quellen und Nachweise

ORD-Eintrag
ord-c15a27e838fa40b2808258ec8aff4935
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259332

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