Pivaloylacetonitrile is a crucial intermediate for the synthesis of the isoxazole skeleton of the selective herbicide isouron and for the construction of inhibitors of p38 MAP kinase based on pyrazolyl ureas.
The current method of synthesis is based on the nucleophilic substitution of halogen of 1-chloro- or 1-bromopinacolone by alkali metal cyanide in protic solvents.
In the course of substitution reaction occurs but the 2-tert-butyloxirane-2-carbonitrile as a side-product in an amount of 20-35% and by-products of the condensation reaction of the corresponding 1-halopinacolone and emerging pivaloylacetonitrile, all due to non-selective action of cyanide.
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