Hydrochloric Acid → Bicine

HRID 439597

Reaction equation

HRID 439597 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

HCID 8761Bicine

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9bbd79bac8864bbfb2a8a012701b0649
Source dataset
uspto-grants-1996_05
Patent number
US05514808

Linked notes

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