Definition
ChEBI: An oxazolidinone that is N-(2,6-dimethylphenyl)-2-methoxyacetamide in which the amide hydrogen is replaced by a 2-oxo-1,3-oxazolidin-3-yl group. A systemic fungicide used to treat seeds of a variety of food crops, as well as lawns.
Synthesis
2,6-Dimethylphenylhydrazine reacts with 2-chloroethyl chloroformate under low-temperature (0-10°C) alkaline conditions to generate N-(2-chloroethoxycarbonyl)-N'-(2,6-dimethylphenyl)hydrazine. Subsequently, this intermediate undergoes acylation with methoxyacetyl chloride in solvents such as toluene to generate a further substituted hydrazine intermediate. Finally, under the action of a strong base (such as sodium hydroxide or sodium hydride) and a phase transfer catalyst, an intramolecular condensation cyclization reaction occurs to form a 2-oxo-1,3-oxazolidine ring, yielding Oxadixyl.
