A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile

Popis výsledku anglicky

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

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/TA03010633" target="_blank" >TA03010633: Progresivní udržitelné technologie pro syntézy chemických specialit z oblasti kyanové chemie</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL

ISSN

0030-4948

e-ISSN

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Svazek periodika

46

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

4

Strana od-do

386-389

Kód UT WoS článku

000340134800007

EID výsledku v databázi Scopus

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