Malonic Acid → HCID 131729134, compound

HRID 905494Notes

Reaction equation

HRID 905494 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].C(=O)(O)O.N[NH:13][C:14]([NH2:16])=[NH:15].C(=O)(O)O.[NH2:21][C:22]([NH2:24])=[NH:23]>O>[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([O-:5])=[O:4].[NH2:15][C:14]([NH2:16])=[NH2+:13].[NH2:23][C:22]([NH2:24])=[NH2+:21]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 178513185HCID 178513185, compound

Product 1

HCID 131729134HCID 131729134, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Malonic acid (200.0 g, 1.922 mol) was weighed into a 2-liter beaker with a magnetic stir bar and dissolved in 1500 ml of distilled water. Aminoguanidine bicarbonate (313.9 g, 2.31 mol) and guanidine carbonate (138.5 g, 0.769 mol) were added in portions with stirring as to avoid bubbling over the sides of the beaker due to the evolution of carbon dioxide during the reaction. The reaction was stirred at room temperature overnight (approximately 24 hours). The water was removed from the reaction mixture in vacuo with heating to approximately 90° C. for 4 hours. The product was recovered as a crystalline white solid.

Workup

  1. customto avoid bubbling over the sides of the beaker due to the evolution of carbon dioxide during the reaction
  2. stirringThe reaction was stirred at room temperature overnight (approximately 24 hours)
  3. customThe water was removed from the reaction mixture in vacuo
  4. customThe product was recovered as a crystalline white solid

Sources & evidence

ORD record
ord-8d05435d6af5434cb867b2a6c0d30efc
Source dataset
uspto-grants-2011_09
Patent number
US08012277B2

Reaction notes

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