464934-83-6

Upstream product

• 80311-89-3 4-bromo-N-benzylbenzamide 
• 18600-42-5 4-nitrobenzylamine hydrochloride 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 80311-91-7 N-(4'-bromobenzoyl)-4-hydroxybenzylamine 
• 1197006-53-3 N-((4-bromophenyl)chloromethylene)(4-nitrophenyl)methanamine 

Relevant academic research and scientific papers

Synthesis of bis(2,4-diarylimidazol-5-yl) diselenides from N-benzylbenzimidoyl isoselenocyanates

The reaction of N-benzylbenzamides 6 with SOCl2 under reflux gave the corresponding N-benzylbenzimidoyl chlorides 7. Further treatment with KSeCN in dry acetone yielded imidoyl isoselenocyanates 3 (Scheme 2). These compounds, obtained in satisfying yields, proved to be stable enough to be purified and analyzed. Reaction of 3 with morpholine in dry acetone led to the corresponding selenourea derivatives 8. On treatment with Et3N, the 4-nitrobenzyl derivatives of type 3 were transformed into bis(2,4-diarylimidazol-5-yl) diselenides 9 (Scheme 3). This transformation takes place only when the benzyl residue bears an NO2 group and the phenyl group is not substituted with a strong electron-donating group. A reaction mechanism for the formation of 9 is proposed in Scheme 4. The key structures have been established by X-ray crystallography.

AROMATIC HYDROXYLATION OF BENZYLAMIDES BY POTASSIUM SUPEROXIDE

N-benzylamides react with potassium superoxide in benzene in presence of 18-crown-6 ether to give ortho and para hydroxylated products.A mechanism is proposed for this reaction, involving the nucleophilic attack of superoxide anion to amide carbonyl and hydrogen abstraction from benzyle methylene by the substrate-superoxide adduct.