Ethanolamine → N-(2-hydroxyethyl)aminomethylphosphonic acid

HRID 1941540Notes

Reaction equation

HRID 1941540 reaction equation
[CH2:1]=O.[CH2:3]([CH2:5][NH2:6])[OH:4].C([O:10][P:11]([O:16]C(C)C)[O:12]C(C)C)(C)C>C(O)(C)C>[OH:4][CH2:3][CH2:5][NH:6][CH2:1][P:11](=[O:16])([OH:12])[OH:10]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 712FormaldehydeHCID 8304Triisopropyl phosphite

Product 1

HCID 10942688N-(2-hydroxyethyl)aminomethylphosphonic acidYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of paraformaldehyde (4.0 g, 0.122 mole), ethanolamine (12 g, 0.2 mole), triisopropylphosphite (20.9 g, 0.1 mole) and 50 mL of isopropanol was stirred at 90° C. for 16 hours. The isopropanol was removed under vacuum and 50 mL of conc. HCl was added in one portion. The solution was heated at reflux for 6 hours after which time it was assayed by 31P-NMR. N-(2-Hydroxyethyl)aminomethylphosphonic acid was obtained in 78% yield.

Workup

  1. customThe isopropanol was removed under vacuum and 50 mL of conc. HCl
  2. additionwas added in one portion
  3. temperatureThe solution was heated
  4. temperatureat reflux for 6 hours after which time it

Sources & evidence

ORD record
ord-76648cb7510e414997a36de3e68006b6
Source dataset
uspto-grants-1997_12
Patent number
US05703273

Reaction notes

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