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Triuret

Triuret is an organic compound with the formula (H<sub>2</sub>NC(O)NH)<sub>2</sub>CO. It is a product from the pyrolysis of urea. Triuret is a colorless, crystalline, hygroscopic solid, slightly soluble in cold water or ether, and more soluble in hot water. It is a planar molecule. The central carbonyl is hydrogen-bonded to both terminal amino groups.

Synthesis

The compound is typically prepared by heating thin layers of urea, the thin layers facilitating escape of ammonia:

3 (H<sub>2</sub>N)<sub>2</sub>CO → [H<sub>2</sub>NC(O)NH]<sub>2</sub>CO + 2 NH<sub>3</sub>

It can also prepared by treatment of urea with phosgene:

2 (H<sub>2</sub>N)<sub>2</sub>CO + COCl<sub>2</sub> → [H<sub>2</sub>NC(O)NH]<sub>2</sub>CO + 2 HCl

A similar synthesis employs urea and dimethyl carbonate with potassium methoxide as a catalyst:

2 (H<sub>2</sub>N)<sub>2</sub>CO + CO(OCH<sub>3</sub>)<sub>2</sub> → [H<sub>2</sub>NC(O)NH]<sub>2</sub>CO + 2 MeOH

The original synthesis entailed oxidation of uric acid with hydrogen peroxide.

Triuret is a complicating by-product in the industrial synthesis of melamine from urea.

Related compounds

References