Reaction #992695

ord-3a1b04a135ae49119311cf305d8c8721

Reaction equation

O=C(O)CN(CC(=O)O)CC(=O)O
Nitrilotriacetic acid
N=C(N)NN.O=C(O)O
Aminoguanidine bicarbonate
O=C=O
carbon dioxide
→
NNC(N)=[NH2+].NNC(N)=[NH2+].NNC(N)=[NH2+].O=C([O-])CN(CC(=O)[O-])CC(=O)[O-]
Tris(aminoguanidinium) Nitrilotriacetate

Reactants

O=C(O)CN(CC(=O)O)CC(=O)O
Nitrilotriacetic acid
N=C(N)NN.O=C(O)O
Aminoguanidine bicarbonate
O=C=O
carbon dioxide

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe water was removed in vacuo
  2. 2
    Temperaturewith heating to approximately 90° C
  3. 3
    OtherThe product was isolated as a white solid

Procedure

Nitrilotriacetic acid (1.0 g, 5.23 mmol) was dissolved in 10 ml of distilled water. Aminoguanidine bicarbonate (2.14 g, 15.69 mmol) was added in portions at room temperature (carbon dioxide gas was evolved) and the reaction was stirred at room temperature for three days. The water was removed in vacuo with heating to approximately 90° C. The product was isolated as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08012277B2uspto-grants-2011_09