P-Nitrobenzamide

Aliphatic and aromatic carboxamides, with the exception of p-nitrobenzamide, are dehydrated in this way in high yield. Acid-labile protective groups such as tetra-hydropyranyl and tert-butyldimethylsilyl ether and base-sensitive compounds are not attacked. A,A -Sulfinyldi-1,2,4-triazole, easily prepared from thionylchloride and triazole [THF, (C2H5)3N, 0 °C, 1 h] in 85-95% yield, was used without further purification. 

A comparison of structures of V-methyl-V-nitroso-p-nitrobenzamide, N,N -dimethyl-V-nitrosourea, V-methyl-V-nitrosourea, 2-nitroso-2-azabicyclo[2.2.2]octan-3-one to those of V-methyl-V -nitro-V-nitrosoguanidine and V,V -dimethyl-V"-cyano-V-nitrosoguanidine shows that the N—N and C—NNO bond lengths in the nitroguanidines44 are similar to those found in the nitrosoamides, but that the corresponding bonds in... 

Amides containing nitro groups are reduced to diamino compounds with alane. A, A -Dimethyl-p-nitrobenzamide, on reduction with lithium aluminum hydride in the presence of sulfuric acid in tetrahydrofuran, gave 98% yield of dimethyl-p-aminobenzylamine [1117]. 

A new and simple synthetic approach to substituted 2-oxazolines starts from readily accessible unfunctionalized aromatic/aliphatic olefins and amides, using t-BuOI, prepared in situ from t-BuOCl and Nal. For instance, alkene 129 reacted with p-nitrobenzamide 130 leading to regioisomeric trans-oxazolines 131a,b with retention of the stereochemistry of the starting olefin <07CC3279>. 

Whiting and Huisgen found identical products from diazonium ions formed in different reaction paths when ion pair dissociation or exchange could reasonably be supposed to have occurred prior to formation of the carbonium ion. A rather different type of study has been carried out by Miller and Stedronsky (1966) (ef. White and Elliger, 1967) who have sought to generate the same diazonium ion pair in the reaction of diphenyldiazomethane with jj-nitrobenzoic acid and in the rearran -ment of N-benzhydryl-N-nitroso-p-nitrobenzamide. 

Product Compositions for the Rearrangement of N-Benzhydryl-N-nitroso-p-nitrobenzamide and the Reaction of DDM with p-Nitrobenzoic Acid... 

Refluxing a solution of l-(p-nitrobenzoyl)-2-benzylaziridine (63) in toluene for 24 hours produced a 91% yield of N-(frflns-cinnamyl)-p-nitrobenzamide (64, equation 10.89). Propose a mechanism for the rearrangement. 

With aromatic amides, hydrolysis prior to rearrangement may occur to such an extent that the yield is lowered seriously. Amides like p-nitrobenzamide, having a substituent which withdraws electrons from O... 

Raycroft MAR, Cimpean L, Neverov AA, Brown RS. Rapid Ni-, Zn- and Cu-ion promoted alcoholysis of N,N-bis(2-picolyl)- and Al,Al-bis((l-H benzimidazol-2-yl) methyl)-p-nitrobenzamides in methanol and ethanol. Inorg Chem. 2014 53(4) 2211 — 2221. 

Actually not even all aromatic weak bases show spectral changes upon protonation. p-Nitrobenzoic acid (11.3) and p-nitrobenzamide (100) do not show changes and there may be others. 

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