A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F14%3A00073284" target="_blank" >RIV/00216224:14310/14:00073284 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1080/00304948.2014.922386" target="_blank" >http://dx.doi.org/10.1080/00304948.2014.922386</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1080/00304948.2014.922386" target="_blank" >10.1080/00304948.2014.922386</a>
Alternative languages
Result language
angličtina
Original language name
A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
Original language description
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 car
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/TA03010633" target="_blank" >TA03010633: Advanced sustainable technologies for fine chemical syntheses based on cyanic chemistry</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
ISSN
0030-4948
e-ISSN
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Volume of the periodical
46
Issue of the periodical within the volume
4
Country of publishing house
US - UNITED STATES
Number of pages
4
Pages from-to
386-389
UT code for WoS article
000340134800007
EID of the result in the Scopus database
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