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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)
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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)
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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)
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skos:notation
| - RIV/00216275:25310/09:00008308!RIV10-MSM-25310___
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http://linked.open...avai/riv/aktivita
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http://linked.open...avai/riv/aktivity
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http://linked.open...iv/cisloPeriodika
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http://linked.open...vai/riv/dodaniDat
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http://linked.open...aciTvurceVysledku
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http://linked.open.../riv/druhVysledku
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http://linked.open...iv/duvernostUdaju
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http://linked.open...titaPredkladatele
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http://linked.open...dnocenehoVysledku
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http://linked.open...ai/riv/idVysledku
| - RIV/00216275:25310/09:00008308
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - 5-amino-4-chloro-2; 7-dimethyl-1H-benzimidazole (en)
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http://linked.open.../riv/klicoveSlovo
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http://linked.open...odStatuVydavatele
| - GB - Spojené království Velké Británie a Severního Irska
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http://linked.open...ontrolniKodProRIV
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http://linked.open...i/riv/nazevZdroje
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http://linked.open...in/vavai/riv/obor
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http://linked.open...ichTvurcuVysledku
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http://linked.open...cetTvurcuVysledku
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http://linked.open...UplatneniVysledku
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http://linked.open...v/svazekPeriodika
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http://linked.open...iv/tvurceVysledku
| - Růžička, Aleš
- Ventura, Karel
- Drabina, Pavel
- Panov, Illia
- Sedlák, Miloš
- Kopřivová, Radka
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http://linked.open...n/vavai/riv/zamer
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issn
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number of pages
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http://localhost/t...ganizacniJednotka
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