223787-58-4

Basic information

• Product Name: N-{2-[2-(2-bromo-phenyl)-ethyl]-5-chloro-phenyl}-formamide
• Synonyms: N-{2-[2-(2-bromo-phenyl)-ethyl]-5-chloro-phenyl}-formamide
• CAS NO: 223787-58-4
• Molecular Weight: 338.631
• Mol File: 223787-58-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-{2-[2-(2-bromo-phenyl)-ethyl]-5-chloro-phenyl}-formamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{2-[2-(2-bromo-phenyl)-ethyl]-5-chloro-phenyl}-formamide(223787-58-4)
• EPA Substance Registry System: N-{2-[2-(2-bromo-phenyl)-ethyl]-5-chloro-phenyl}-formamide(223787-58-4)

Safety Data

• Hazardous Substances Data: 223787-58-4(Hazardous Substances Data)

Upstream product

• 52311-59-8 4-chloro-2-nitrobenzyl bromide 
• 52311-60-1 4-chloro-2-nitrobenzylphosphonic acid diethyl ester 
• 89-59-8 4-chloro-2-nitrotoluene 
• 64-18-6 formic acid 
• 223787-53-9 2-[2-(2-bromo-phenyl)-ethyl]-5-chloro-phenylamine 

Downstream Products

• 32943-25-2 3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine 

Relevant articles and documents

Synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines; key synthons in syntheses of pharmaceutically active compounds

Substituted 10,11-dihydro-5H-dibenz[b,f]azepines are key synthons in the syntheses of a number of pharmaceutically active compounds such as imipramine, chlorimipramine, and desimipramine analogues. A facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines is described, starting out from commercially available 2-bromotoluenes or 2-nitrotoluenes. Initial α-bromination with N-bromosuccinimide and subsequent reaction with triethylphosphite afforded the corresponding benzyl phosphonic ester derivatives. After reaction with benzaldehyde derivatives, the expected Horner-Emmons reaction products were obtained. Hydrogenation gave the amino derivatives which were transformed into the corresponding formamides. Under Goldberg conditions [1], the final ring closing step was performed to give the substituted 10,11-dihydro-5H-dibenz[b,f]azepines in 46-75% yield.