Method for the synthesis of 3-r-1,4,2-dioxazol-5-ones technical field
AssigneeTesla Motors Canada ULC
InventorsDavid S. Hall, Jeffery Raymond Dahn, Toren Hynes
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Abstract
Provided are methods of preparing 3-R-1,4,2-dioxazol-5-one compounds using convenient and efficient methods. Also provided are 3-R-1,4,2-dioxazol-5-one compounds produced using the methods described.
Claims29
A method of preparing a 3-R-1,4,2-dioxazol-5-one compound, comprising:
- combining hydroxylamine, or a salt thereof, and a first organic solvent to form a first reaction mixture;
- adding an R-substituted acyl halide to the first reaction mixture to form a second reaction mixture;
- adding N,N′-carbonyldiimidazole to the second reaction mixture to form a third reaction mixture;
- and
- obtaining a 3-R-1,4,2-dioxazol-5-one compound from the third reaction mixture, wherein the first, second and third reaction mixtures are formed by a one-pot method.
The method of claim 23, wherein the R-substituted acyl chloride is selected from the group consisting of benzoyl chloride, 2-thiophenecarbonyl chloride, p-toluoyl chloride, 2-naphthoyl chloride, p-fluorobenzoyl chloride, m-fluorobenzoyl chloride, o-fluorobenzoyl chloride, p-methoxybenzoyl chloride, p-nitrobenzoyl chloride, m-nitrobenzoyl chloride, o-nitrobenzoyl chloride, p-teraphthaloyl chloride, p-chlorobenzoyl chloride, m-chlorobenzoyl chloride, o-chlorobenzoyl chloride, and combinations thereof.
The method of claim 27, wherein the third organic solvent is selected from the group consisting of ethyl acetate, tetrahydrofuran, and combinations thereof.
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A method of preparing a 3-R-1,4,2-dioxazol-5-one compound, comprising:
- combining hydroxylamine hydrochloride, triethylamine, N,N-dimethylformamide (DMF) and ethyl acetate to form a first reaction mixture, wherein the first reaction mixture is cooled to 0° C.;
- adding an R-substituted acyl chloride and additional triethylamine to the first reaction mixture to form a second reaction mixture, wherein the second reaction mixture is warmed to room temperature;
- adding N,N′-carbonyldiimidazole to the second reaction mixture to form a third reaction mixture;
- adding an acid to the third reaction mixture to form a quenched reaction mixture;
- and
- obtaining a 3-R-1,4,2-dioxazol-5-one compound from the quenched reaction mixture, wherein the first, second, third and quenched reaction mixtures are formed by a one-pot method.
Dependencies are inferred from the claim text.