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Templated Organic Synthesis. Edited by F. Diederich (diederich@org.chem.ethz.ch) and Peter J. Stang (stang@chemistry.chem.utah.edu). Wiley-VCH: Weinheim. 1999. XX+411 pp. 268 DM. ISBN 3-527-29666-2
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Synthesis of the Formal Diels-Alder Adducts of N-substituted Dehydromaleimides and Anthracene
Molecules 2000, 5(2), 189-194; doi:10.3390/50200189
Article

Synthesis of N-(2-Cyanophenyl)chloromethanimidoyl Chloride

* , ,  and
Department of Organic Chemistry, Faculty of Science, Masaryk University, CZ-611 37 Brno, Czech Republic
* Author to whom correspondence should be addressed.
Received: 9 December 1999 / Accepted: 5 January 2000 / Published: 24 February 2000
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Abstract

N-(2-Cyanophenyl)chloromethanimidoyl chloride (3) was prepared from 2-isothiocyanatobenzonitrile by the reaction with sulfuryl chloride or gaseous chlorine in an inert solvent. It was found that N-(2-cyanophenyl)chloromethanimidothioic chloride (2) and bis[N-(cyanophenyl)chloromethanimidoyl] sulfide (7) are intermediates of this reaction. The chloride 3 was obtained also by a three-component one-pot reaction of N-(2-cyanophenyl)-formamide in the present of thionyl chloride and sulfuryl chloride. (2-Cyanophenyl)-(1-{[(2-cyanophenyl)-imino]methoxy}methylidene)ammonium chloride (6) was detected as a by-product of this reaction. Identity of all reaction products was confirmed by GC-MS, FTIR, 1H and 13C NMR spectroscopy.
Keywords: N-(2-cyanophenyl)chloromethanimidoyl chloride; 2-isothiocyanatobenzonitrile; N-(2-cyanophenyl)formamide N-(2-cyanophenyl)chloromethanimidoyl chloride; 2-isothiocyanatobenzonitrile; N-(2-cyanophenyl)formamide
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Pazdera, P.; Divišová, H.; Havlišová, H.; Borek, P. Synthesis of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. Molecules 2000, 5, 189-194.

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