Benzamides nitro

The need of the acylurea site participating in intermolecular hydrogen bonding (cf. Figs. 11 and 12) for the complex formation is exemplified by the fact that a 1 1 mixture of JV-(p-dimethylaminophenyl)phenylacetamide (21) and JV-isobutyl-p-nitro-benzamide (22) gives no crystalline complexes under the same conditions as with 19 and 20. The trend of the complex formation often changes, when the combinations of R7 and R8 are reversed 35). 

Zur Reduktion entsprechender Carbamidsaure-ester s. S. 350f. 4-Nitro-benzamide werden mit Aluminiumhydrid zu 4-Amino-benzylaminen reduziert (s. S. 475). 

In contrast to the aforementioned monosubstitutions, much less is known about the effect of disubstitution. It appears that such benzamides are resistant to hydrolysis. The metabolic fate of nitromide (3,5-dinitrobenzamide, 4.63), a chicken-feed additive for the prevention of coccidosis, was investigated in rats. The metabolite 3-amino-5-nitrobenzoic acid (4.64), formed by ni-tro reduction and hydrolysis, was excreted in only trace amounts. Nitromide was metabolized mainly via nitro reduction [36], Similarly, no hydrolysis was... 

Procainamide Procainamide, 4-amino-N-[2-(diethylamino)ethyl]benzamide (18.1.3), is synthesized by reacting 4-nitrobenzoic acid chloride with N,N-diethylethylendiamine and subsequent reduction of the nitro gronp of the resnlting 4-nitro-N-[2-(diethylamino)ethyl]ben-zamide (18.1.2) into an amino group [8,9]. 

Beim Hofmann-Abbau von 3-Methoxy-2-nitro-benzamid erhalt man fiber 3-Methoxy-2-ni-tro-anilin 4-Methoxy-benzofurazan-l-oxid125 ... 

To facilitate the nitro group displacement reaction, the thioethers 7, obtained by treatment of difluoride 6 with thiols, were oxidized with 3-chloroperbenzoic acid to afford the corresponding sulfones 8 (Fig. 4). The resulting sulfones 8 showed the expected high reactivity toward nucleophiles, as demonstrated by the efficient displacement of both the second fluoride and the nitro group with two different aliphatic amines to yield the highly substituted benzamides 10. 

To the solution of 4-nitro-benzoylchloride the diethyl aminoethane and sodium ethoxide were added and mixed. As a result of reaction a N-(2-diethylamino-ethyl)-4-nitro-benzamide was obtained. 

The method is of great value in dealing with substances which are sensitive to strong acids or bases, such as o-nitro- and amino-benzaldehydes, nitro- and amino-benzamides and benzoylureas, and is also of service in the preparation of other ammo acids. 

Nitro-piperazin-1 -yl-N- (tricycle [3.3.1. ] dec-1 -ylmetbyl-benzamide bydrogen chloride... 

Tentagel-graft-(2,6-di-benzylbromo-3-nitro-benzamide)lysine... 

The observed stereospecificity of the reaction in the conversion of l-(p-nitro-benzoyl)-2-benzylaziridine in refluxing toluene into A -( ra/w)-cinnamyl-p-nitro-benzamide is best explained in terms of an intramolecular reaction mechanism in which cis elimination of a proton is concerted with opening of the aziridine ring (A)... 

This makes some sense based upon electron density and reactivity considerations, but, the nitro group occupies a much larger space than the pyridine nitrogen lone pair of electrons. In order to test this equivalence, we prepared some 3-nitro-2-phenoxy-benzamides for comparison to their pyridine analogs. Two of these are shown in Table IV. 

As can be seen from Table IV, the nitrophenyl analogs of the nicotinamides are inactive. Interestingly, the 2-(3-trifluoromethylphenyl ) benzamides (compound IV minus the nitro group) were moderate herbicides (less than 50% weed control at 1 lb). These compounds are also bleaching herbicides as are the well known 3-phenoxybenzamides. The 3-phenoxybenzamides are also known to be inhibitors of phytoene desaturase (11). 

Bei der Bildung der 2-Amino-benzamide aus 2-Nitro-benzonitrilen wird das Sauer-stoff-Atom vom intermediar-gebildeten N-Phenyl-hydroxylamin infolge voriibergehen-der Cyclisierung zum 3-Amino-l,2-benzoxazol auf die Cyan-Gruppe iibertragen1 2. 

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