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  • 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. Our sophisticated solution of this problem is based on the addition of a catalytic amount of alkali iodide, leading to the suppression of undesirable side reactions and to obtain pivaloylacetonitrile in 95% yield with a purity of 99%. Explanation of the effect of added alkali iodide to increase the selectivity of the process being carried out.
  • 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. Our sophisticated solution of this problem is based on the addition of a catalytic amount of alkali iodide, leading to the suppression of undesirable side reactions and to obtain pivaloylacetonitrile in 95% yield with a purity of 99%. Explanation of the effect of added alkali iodide to increase the selectivity of the process being carried out. (en)
Title
  • A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
  • A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile (en)
skos:prefLabel
  • A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
  • A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile (en)
skos:notation
  • RIV/00216224:14310/14:00073284!RIV15-TA0-14310___
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  • P(TA03010633)
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  • 4
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  • 1177
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  • RIV/00216224:14310/14:00073284
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  • Nitriles; Synthesis of Organic Molecules; Catalysis; Green and Sustainable Chemistry; Waste Management AT SOURCE (en)
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  • US - Spojené státy americké
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  • [940E382480E0]
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  • ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
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  • 46
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  • Pazdera, Pavel
  • Šimbera, Jan
  • Zelinka, Karel
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  • 000340134800007
issn
  • 0030-4948
number of pages
http://bibframe.org/vocab/doi
  • 10.1080/00304948.2014.922386
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  • 14310
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