51223-59-7

Usage

InChI:InChI=1/C8H9ClN2O/c1-5(12)11-8-3-2-6(9)4-7(8)10/h2-4H,10H2,1H3,(H,11,12)

Upstream product

• 881-51-6 N-(4-chloro-2-nitrophenyl)-acetamide 
• 539-03-7 N-(4-chlorophenyl)acetamide 

Downstream Products

• 21639-42-9 acetic acid-(4-chloro-2-phenylazo-anilide) 
• 84445-86-3 1-(5-Chloro-2-mercapto-benzoimidazol-1-yl)-ethanone 
• 25369-78-2 5-chloro-1H-benzoimidazole-2-thiol 
• 86569-38-2 N-acetyl-N'-butyryl-4-chloro-1,2-phenylenediamine 
• 2818-69-1 5-chloro-2-methyl-1H-benzimidazole 
• 86569-36-0 N,N'-diacetyl 4-chloro-1,2-phenylenediamine 
• 86569-37-1 N-acetyl-N'-propionyl-4-chloro-1,2-phenylenediamine 
• 113001-02-8 N-(4-Chloro-2-{[1-(2-nitro-phenyl)-meth-(Z)-ylidene]-amino}-phenyl)-acetamide 
• 21639-43-0 4-chloro-2-phenylazo-aniline 
• 113001-15-3 2-amino-6-chloro-3-(5-chloro-2-nitrophenyl)quinoxaline 
• 113001-04-0 N-(4-Chloro-2-{[1-(5-chloro-2-nitro-phenyl)-meth-(Z)-ylidene]-amino}-phenyl)-acetamide 

Relevant academic research and scientific papers

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.

o-Nitrobenzylidene Compounds. Part 4. The Cyanide-induced Cyclisation of o-Acetamido-N-(o-nitrobenzylidene)anilines: an Improved Route to Quinoxalinocinnolines

Cyclisation of o-acetamido-N-(o-nitrobenzylidene)anilines (7) with potassium cyanide in methanol (preferably under nitrogen) leads in most cases to quinoxalinocinnolines (6) of unambiguous substitution pattern.In some cases, cyclisation appears to be incomplete, and 2-amino-3-(o-nitrophenyl)quinoxalines (11) are obtained as by-products; in certain cases quinoxalinocinnoline 5-oxides (10) are also detected.These by-products are assumed to result from oxidation of intermediates in the cyclisation process (7) ----> (6).

SYNTHESIS AND PESTICIDAL ACTIVITY OF N,N'-DIACYL DERIVATIVES OF 4-CHLORO-1,2-PHENYLENDIAMINE

The acylation of 2-aminoacyl-chloroanilines with acid anhydrides has given N,N'-diacyl derivatives of 4-chloro-1,2-phenylenediamine.Their fungicidal activities have been investigated.It has been shown that in cotton plants they are converted into 2-alkyl-5-chlorobenzimidazoles.

Synthesis of N-Acetylbenzimidazole Derivatives

For the structure determination of thiazolobenzimidazol-3(2H)-one derivatives (2 or 3) they were converted to the corresponding 1-acetylbenzimidazoles (4) by desulfurization.The latter compounds (4) were alternatively prepared by the cyclization of 2-aminoacetanilide derivatives (5) with CS2 in dimethylformamide (DMF), followed by desulfurization with Raney Ni.However, the reactions of 5 with ethyl orthoformate/H2SO4 in DMF gave a mixture of 4 and its acetyl-rearranged product (7).Keywords-acetyl group; rearrangement; thiazolobenzimidazol-3(2H)-one; N-acetylbenzimidazoles; ethyl orthoformate; carbon disulfide; desulfurization