Ethanolamine → N-(2-hydroxyethyl)aminomethylphosphonic acid

HRID 1450730Notes

Reaction equation

HRID 1450730 reaction equation
[CH2:1]=O.[CH2:3]([CH2:5][NH2:6])[OH:4].C([O:10][P:11]([O-:16])[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 21884976Phosphorous acid, bis(1-methylethyl) ester

Product 1

HCID 10942688N-(2-hydroxyethyl)aminomethylphosphonic acidYield 33%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of paraformaldehyde (4.0 g, 0.13 mol), ethanolamine (6 mL, 0.097 mol), diisopropylphosphite (17 g, 0.1 mol) and 50 ml of isopropanol was stirred at 120° C. for 16 hours. The solution was concentrated to dryness and 17 ml of 50% NaOH was added. The solution was heated at reflux for 16 h, cooled to room temperature and concentrated under vacuum. Water (100 mL) was added to homogenize the mixture. The reaction was analyzed by 31P NMR in D2O at pH=0.8. N-(2-Hydroxylethyl)aminomethylphosphonic acid was obtained in 33% yield.

Workup

  1. concentrationThe solution was concentrated to dryness and 17 ml of 50% NaOH
  2. additionwas added
  3. temperatureThe solution was heated
  4. temperatureat reflux for 16 h
  5. concentrationconcentrated under vacuum
  6. additionWater (100 mL) was added

Sources & evidence

ORD record
ord-7510ef2a340c4e83aab1ccd14a5bd7a0
Source dataset
uspto-grants-1997_02
Patent number
US05602276

Reaction notes

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