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n,n-1,2-phenylenebis[4-(chloromethyl)benzamide]n,nu20191,2-phenylenebis[4 -(chloromethyl)苯甲酰胺)
Molbank 2010, M705; doi:10.3390/M705
OPEN ACCESS
molbank
ISSN 1422-8599
/journal/molbank
Short Note
N,N-1,2-Phenylenebis[4-(chloromethyl)benzamide]
Jürgen Bachl 1 and David D. Díaz 1,2,*
1 Institut für Organische Chemie, Universität Regensburg, Universitätsstr 31, 93040 Regensburg,
Germany
2 ICMA, CSIC-Universidad de Zaragoza, Pedro Cerbuna 12, 50009 Zaragoza, Spain
* Author to whom correspondence should be addressed;
E-Mail: David.Diaz@chemie.uni-regensburg.de.
Received: 8 October 2010 / Accepted: 1 November 2010 / Published: 4 November 2010
Abstract: N,N-1,2-Phenylenebis[4-(chloromethyl)benzamide] (3) was obtained in 61%
yield by nucleophilic acyl substitution of 4-(chloromethyl)benzoyl chloride (2) with 1,2-
phenylenediamine (1) under basic conditions. The title compound was characterized by
FT-IR, 1H NMR, 13C NMR, low- and high-resolution EI-MS, and melting point.
Keywords: o-phenylenediamine; benzamide; nucleophilic acyl substitution
Substituted benzamides have been in clinical use for many years as anti-emetics, anti-arrhythmics,
neuroleptics, and/or anti-psychotics in the treatment of various disorders [1]. They also constitute
versatile intermediates for the synthesis of anti-tumor and anti-inflammatory agents [2], protease
inhibitors [3], dyes [4], and have been extensively used as sensitizers for radio- or chemotherapies [5].
On the other hand, benzyl chloride derivatives are widely used as synthetic building blocks. They
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