2,4-Oxazolidinedione

2,4-Oxazolidinedione is a chemical compound that belongs to the class of organic compounds known as oxazolidinediones. It is a heterocyclic compound with a five-membered ring structure containing an oxygen atom, a nitrogen atom, and two carbonyl groups. The compound is also known as oxazolidine-2,4-dione or 2,4-dioxazolidine.

Structure and Properties

The structure of 2,4-oxazolidinedione consists of a five-membered ring with an oxygen atom at the 1-position, a nitrogen atom at the 3-position, and two carbonyl groups at the 2- and 4-positions. This structure is similar to that of other heterocyclic compounds such as pyrazolidinedione and imidazolidinedione.

The compound is a solid at room temperature and has a molecular weight of 114.07 g/mol. It has a melting point of 210-212 °C and a boiling point of 250 °C. The compound is soluble in water and most organic solvents.

Synthesis

2,4-Oxazolidinedione can be synthesized from urea and glyoxylic acid in the presence of a base such as sodium hydroxide. The reaction proceeds via a condensation reaction, with the elimination of water to form the oxazolidinedione ring.

Applications

2,4-Oxazolidinedione is used as a building block in the synthesis of various pharmaceutical compounds. It is a key intermediate in the synthesis of antibiotics such as linezolid and tedizolid, which are used to treat bacterial infections. The compound is also used in the synthesis of antidiabetic drugs such as pioglitazone and rosiglitazone, which are used to treat type 2 diabetes.

Safety and Toxicity

As with all chemical compounds, 2,4-oxazolidinedione should be handled with care. It may cause irritation to the skin and eyes, and may be harmful if swallowed or inhaled. Appropriate safety measures should be taken when handling this compound.

See Also

• Oxazolidinone
• Heterocyclic compound
• Pharmaceutical chemistry