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US 9,040,711 B2Granted
Processes for the preparation of 3,5-disubstituted-1,2,4-oxadiazoles
AssigneeMonsanto Technology LLC
InventorsWilliam Harold Miller, Charles Richard Graham, David Louis Brown
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Abstract
Provided herein are processes for the preparation of 3,5-disubstituted-1,2,4-oxadiazoles and salts thereof comprising reacting a N-hydroxyamidine with an acyl chloride in a reaction mixture comprising a water-immiscible organic solvent and an aqueous base at relatively low reaction temperatures.
Claims45
A process for preparing a 3,5-disubstituted 1,2,4-oxadiazole of Formula (Ia) or (Ib), or a salt thereof,
- the process comprising reacting an N-hydroxyamidine of Formula (IIa) or (IIb), respectively, or a tautomeric form thereof,
- with an acyl chloride of Formula (IIIa) or (IIIb), respectively,
- in a reaction mixture comprising an organic phase and an aqueous phase,
- wherein the reaction mixture comprises a water-immiscible organic solvent and an aqueous base,
- wherein the temperature of the reaction mixture is no greater than about 85° C.;
- and wherein Ar1 is selected from the group consisting of phenyl, pyridyl, pyrazyl, oxazolyl or isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halogen, CF3, CH3, OCF3, OCH3, CN and C(H)O;
- and
- Ar2 is selected from the group consisting of is thienyl, furanyl, oxazolyl or isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH3, and OCF3.
5 more elements
Dependencies are inferred from the claim text.