Hydrochloric Acid → HCID 10198016, compound

HRID 1489783Notes

Reaction equation

HRID 1489783 reaction equation
Br[C:2]([CH3:8])([CH3:7])[C:3]([O:5]C)=[O:4].[OH:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][OH:15].[OH-].[Na+].Cl>C(O)CC.C(N(CC)CC)C>[OH:9][CH2:10][CH2:11][N:12]([C:2]([CH3:8])([CH3:7])[C:3]([OH:5])=[O:4])[CH2:13][CH2:14][OH:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8113DiethanolamineHCID 14798Sodium Hydroxide2×HCID 90097Methyl 2-bromo-2-methylpropionate

Product 1

HCID 10198016HCID 10198016, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8471TriethylamineSolvent

Procedure

Methyl 2-bromo-2-methylpropanoate (181.04 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 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 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, 2-[N,N-bis-(2-hydroxyethyl)-amino]-2-methylpropanoic 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 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. filtration2-[N,N-bis-(2-hydroxyethyl)-amino]-2-methylpropanoic acid separates and is collected by filtration
  12. washis washed with a 50% aqueous ethanol
  13. customdried

Sources & evidence

ORD record
ord-32beb86f873e47288db8be5775205b2d
Source dataset
uspto-grants-1997_10
Patent number
US05679711

Reaction notes

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