About: 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

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About: 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 Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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. H-1, C-13 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. 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. H-1, C-13 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. (en)
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 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 (en)
skos:prefLabel	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 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 (en)
skos:notation	RIV/00216275:25310/09:00008308!RIV10-MSM-25310___
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM0021627501)
http://linked.open...iv/cisloPeriodika	2
http://linked.open...vai/riv/dodaniDat	2010
http://linked.open...aciTvurceVysledku	Ventura, Karel Růžička, Aleš Sedlák, Miloš Drabina, Pavel
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Pardubice / Fakulta chemicko-technologická
http://linked.open...dnocenehoVysledku	308707
http://linked.open...ai/riv/idVysledku	RIV/00216275:25310/09:00008308
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	5-amino-4-chloro-2; 7-dimethyl-1H-benzimidazole (en)
http://linked.open.../riv/klicoveSlovo	5-amino-4-chloro-2 7-dimethyl-1H-benzimidazole
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[7904B3350087]
http://linked.open...i/riv/nazevZdroje	Dyes and Pigments
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...UplatneniVysledku	2009
http://linked.open...v/svazekPeriodika	81
http://linked.open...iv/tvurceVysledku	Růžička, Aleš Ventura, Karel Drabina, Pavel Panov, Illia Sedlák, Miloš Kopřivová, Radka
http://linked.open...n/vavai/riv/zamer	Aimed preparation of special compounds and materials and investigation of their physical and chemical properties and supramolecular structures
issn	0143-7208
number of pages	6 (xsd:int)
http://localhost/t...ganizacniJednotka	25310

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