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Statements

Subject Item
n2:RIV%2F00216224%3A14310%2F14%3A00073284%21RIV15-TA0-14310___
rdf:type
skos:Concept n14:Vysledek
dcterms: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 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.
dcterms:title
A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
skos:prefLabel
A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
skos:notation
RIV/00216224:14310/14:00073284!RIV15-TA0-14310___
n3:aktivita
n18:P
n3:aktivity
P(TA03010633)
n3:cisloPeriodika
4
n3:dodaniDat
n4:2015
n3:domaciTvurceVysledku
n5:9756078 n5:9343350
n3:druhVysledku
n16:J
n3:duvernostUdaju
n13:S
n3:entitaPredkladatele
n15:predkladatel
n3:idSjednocenehoVysledku
1177
n3:idVysledku
RIV/00216224:14310/14:00073284
n3:jazykVysledku
n7:eng
n3:klicovaSlova
Nitriles; Synthesis of Organic Molecules; Catalysis; Green and Sustainable Chemistry; Waste Management AT SOURCE
n3:klicoveSlovo
n9:Nitriles n9:Waste%20Management%20AT%20SOURCE n9:Synthesis%20of%20Organic%20Molecules n9:Green%20and%20Sustainable%20Chemistry n9:Catalysis
n3:kodStatuVydavatele
US - Spojené státy americké
n3:kontrolniKodProRIV
[940E382480E0]
n3:nazevZdroje
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
n3:obor
n8:CC
n3:pocetDomacichTvurcuVysledku
2
n3:pocetTvurcuVysledku
3
n3:projekt
n17:TA03010633
n3:rokUplatneniVysledku
n4:2014
n3:svazekPeriodika
46
n3:tvurceVysledku
Zelinka, Karel Šimbera, Jan Pazdera, Pavel
n3:wos
000340134800007
s:issn
0030-4948
s:numberOfPages
4
n11:doi
10.1080/00304948.2014.922386
n19:organizacniJednotka
14310