Reaction #992693

ord-2ba0fedd47514f2ea231865f164fe779

Reaction equation

O=C(O)CC(O)C(=O)O
DL-Malic acid
N=C(N)NN.O=C(O)O
Aminoguanidine bicarbonate
O=C=O
carbon dioxide
→
NNC(N)=[NH2+].NNC(N)=[NH2+].O=C([O-])CC(O)C(=O)[O-]
Bis(aminoguanidinium) DL-Malate

Reactants

O=C(O)CC(O)C(=O)O
DL-Malic 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. for 4 hours
  3. 3
    OtherThe product was isolated as a white solid

Procedure

DL-Malic acid (2.0 g, 14.92 mmol) was dissolved in 5 ml of distilled water. Aminoguanidine bicarbonate (4.06 g, 29.83 mmol) was added in portions at room temperature (carbon dioxide gas was evolved) and the reaction was stirred at room temperature for 18 hours. The water was removed in vacuo with heating to approximately 90° C. for 4 hours. The product was isolated as a white solid.

Source

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