Hydrochloric Acid → Bicine

HRID 1899865

Reaktionsgleichung

Reaktionsgleichung von HRID 1899865
Br[CH2:2][C:3]([O:5]C)=[O:4].[OH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][OH:13].C(N(CC)CC)C.[OH-].[Na+].Cl>C(O)CC>[OH:7][CH2:8][CH2:9][N:10]([CH2:2][C:3]([OH:5])=[O:4])[CH2:11][CH2:12][OH:13]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8113DiethanolamineHCID 8471TriethylamineHCID 14798Sodium Hydroxide2×HCID 60984Methyl bromoacetate

Produkt 1

HCID 8761Bicine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

Methyl bromoacetate (152.98 grams, 1 mole) is dissolved in 1-propanol (500 ml.) and bis-(2-hydroxyethyl)amine (105.14 grams, 2 moles) and triethylamine (111.1 grams, 1.1 moles) are added and the mixture is stirred and heated at reflux for 3 hours. The mixture is treated with 10 normal sodium hydroxide (110 ml., 1.1 moles) and the solvents are removed by distillation in vacuo. The residue is filtered and the solid is washed with 1-propanol. The combined filtrates are dissolved in ethanol (400 ml) and 10 normal sodium hydroxide (130 ml, 1.3 moles) is added. The mixture is stirred and heated at reflux for 3 hours. The mixture is acidified with 12 normal hydrochloric acid (108 ml, 1.3 moles). Upon cooling, N,N-bis-(2-hydroxyethyl)aminoacetic acid separates and is collected by filtration, and is washed with a 50% aqueous ethanol and dried.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customthe solvents are removed by distillation in vacuo
  4. filtrationThe residue is filtered
  5. washthe solid is washed with 1-propanol
  6. dissolutionThe combined filtrates are dissolved in ethanol (400 ml)
  7. stirringThe mixture is stirred
  8. temperatureheated
  9. temperatureat reflux for 3 hours
  10. temperatureUpon cooling
  11. filtrationN,N-bis-(2-hydroxyethyl)aminoacetic acid separates and is collected by filtration
  12. washis washed with a 50% aqueous ethanol
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c9d1feae22594834934d43c9bbe30c91
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574050

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