13614-61-4

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 201024-81-9 C,N-diphenylnitrone 
• 93-98-1 N-phenyl benzoyl amide 
• 51293-24-4 N-Phenylbenzonitrilium hexachloroantimonate 
• 14805-58-4 N,N'-dibenzoyl-N,N'-diphenyl-oxalamide 
• 62-53-3 aniline 
• 160693-94-7 benzophenone-(O-benzenesulfonyl oxime ) 
• 124-41-4 sodium methylate 

Downstream Products

• 33345-17-4 N,N-diphenylbenzamidine 
• 65-85-0 benzoic acid 
• 2556-46-9 N,N'-diphenylbenzamidine 

Relevant academic research and scientific papers

Efficient access to polysubstituted amidines, benzimidazoles and pyrimidines from amides

Polysubstituted amidines, benzimidazoles and pyrimidines were synthesized via the electrophilic activation of amides with trifluoromethanesulfonic anhydride and 2-chloropyridine. The one-pot protocol is concise and efficient and the substrates are readily available.

INTERMOLECULAR IMIDOYLATION REACTION OF THE CARBOXAMIDE GROUP

Reactions of N-monosubstituted benzamides with Ph3PBr2 and Et3N in refluxing CH2Cl2 for 0.5 - 5 hours give good yields of N,N'-disubstituted-N-acylamidines.The latter compounds may be regarded as intermolecular N-imidoylation products of the amide group.Under the same reaction conditions, N-monosubstituted amides containing C-H bonds adjacent to the carbonyl function and N-monosubstituted formamides are dehydrated to ketenimines and isonitriles, respectively.Treatment of N-methyl-benzamide with Ph3PBr2 and Et3N leads to the formation of an intermediate whose ir spectrum is consistent with the N,N,N-triethyl-N'-methylbenzamidinium salt structure.A substance with identical spectroscopic characteristics was obtained on treatment of N-methyl-α-bromobenzylideneammonium bromide with Et3N.Products of the reaction of 5- and 6-membered lactams with Ph3PBr2 and Et3N are inactive as imidoylating agents; consequently, these lactams do not undergo self-condensation to N-imidoylation products, but they can participate in the imidoylation reactions as nucleophiles subjected to imidoylation.In contrast to the 5- and 6-membered lactams, ε-caprolactam undergoes self-condensation to the expected N-imidoylation product.Possible mechanistic pathways for the imidoylation reaction of the amide group have been suggested.

The side-chain acylamination of alicyclic nitrones. A new synthesis of an α-amino acid

2,4,4-Trimethyl-Δ1-pyrroline-1- (4) and 2-n-butyl-4,4-dimethyloxazoline-3-oxide (6) are acylaminated in the presence of base at the α-position of the side-chain at C-2 to give 5 and 10, respectively.Ethanolysis of 10 gives the corresponding α-amino ester (11) in good yield