Zobrazit minimální záznam
dc.contributor.author |
Drabina, Pavel |
|
dc.contributor.author |
Panov, Illia |
|
dc.contributor.author |
Sedlák, Miloš |
|
dc.contributor.author |
Růžička, Aleš |
|
dc.contributor.author |
Kopřivová, Radka |
|
dc.contributor.author |
Ventura, Karel |
|
dc.date.accessioned |
2010-10-18T09:57:07Z |
|
dc.date.available |
2010-10-18T09:57:07Z |
|
dc.date.issued |
2009 |
|
dc.identifier.issn |
0143-7208 |
|
dc.identifier.uri |
http://hdl.handle.net/10195/37727 |
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dc.description.abstract |
Commercially delivered 2-chloro-5-methyl-1,4-phenylenediamine (1 metric ton) was not identical to the commonly used dye intermediate; it was found that the material was a pure but not yet described molecule. 1H, 13C NMR, MS, microanalysis and X-ray diffraction showed that the substance was in fact 5-amino-4-chloro-2,7-dimethyl-1H-benzimidazole. The manufacturer's mistake was explained by independent synthesis, which revealed that the key step was nitration of N-(5-chloro-2-methyl-4-nitrophenyl)acetamide giving N-(5-chloro-2-methyl-4,6-dinitrophenyl)acetamide, which requires Fe(III) catalysis. Subsequent reduction of N-(5-chloro-2-methyl-4,6-dinitrophenyl)acetamide with hydrogen and Pd/C catalyst exclusively gives N-(2,4-diamino-3-chloro-6-methylphenyl)acetamide. The ring closure reaction giving 5-amino-4-chloro-2,7-dimethyl-1H-benzimidazole takes place during the reduction with iron. |
eng |
dc.format |
p. 113-118 |
eng |
dc.language.iso |
eng |
|
dc.publisher |
Elsevier |
cze |
dc.relation.ispartof |
Dyes and Pigments. 2009, vol. 81, issue 2 |
eng |
dc.rights |
open access |
eng |
dc.subject |
Dye intermediates |
eng |
dc.subject |
1H-Benzimidazoles |
eng |
dc.subject |
Heterocycles |
eng |
dc.subject |
Nitration |
eng |
dc.subject |
Ferric nitrate |
eng |
dc.subject |
X-ray diffraction |
eng |
dc.title |
The current dye intermediate market - A cautionary tale and detective story; characterization and unambiguous synthesis of 5-amino-4-chloro-2,7-dimethyl-1H-benzimidazole |
eng |
dc.type |
Article |
eng |
dc.peerreviewed |
yes |
eng |
dc.publicationstatus |
postprint |
eng |
dc.identifier.doi |
10.1016/j.dyepig.2008.09.012 |
|
dc.relation.publisherversion |
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TFY-4TMBPTW-1&_user=640852&_coverDate=05%2F31%2F2009&_rdoc=1&_fmt=high&_orig=search&_origin=search&_sort=d&_docanchor=&view=c&_acct=C000032310&_version=1&_urlVersion=0&_userid=640852&md5=6b8f8965426174be9b5331b5bd70c406&searchtype=a |
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