Formic Acid → N-Formyl-N-phosphonomethylglycine

HRID 363810Notes

Reaction equation

HRID 363810 reaction equation
[NH2:1][CH2:2][P:3](=[O:6])([OH:5])[OH:4].O.[C:8]([OH:12])(=[O:11])[CH:9]=O.[CH:13](O)=[O:14]>>[CH:13]([N:1]([CH2:2][P:3]([OH:5])([OH:4])=[O:6])[CH2:9][C:8]([OH:12])=[O:11])=[O:14]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 14017(Aminomethyl)phosphonic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 13920556N-Formyl-N-phosphonomethylglycine

Conditions

Temperature
80 °C

Procedure

Aminomethylphosphonic acid (3.12 g, 0.028 mol) was dissolved in 30 ml of stirred 98% formic acid maintained at 80° C. with an oil bath. Glyoxylic acid hydrate (5.60 g, 0.061 mol) was added to the solution in several portions, resulting in vigorous gas evolution. After one hour, the reaction flask was removed from the oil bath and the solvent removed on a rotary evaporator to afford crude N-formyl-N-phosphonomethylglycine as a viscous yellow oil.

Workup

  1. customresulting in vigorous gas evolution
  2. customthe reaction flask was removed from the oil bath
  3. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-886a68b4fd5b49b8ae35c0efe7027f8b
Source dataset
uspto-grants-1999_02
Patent number
US05874612

Reaction notes

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