54986-47-9

Usage

InChI:InChI=1/C13H9ClN2O/c14-9-6-7-11-12(8-9)16(13(17)15-11)10-4-2-1-3-5-10/h1-8H,(H,15,17)

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 1245611-16-8 5-chloro-2-nitroso-N-phenylbenzenamine 
• 124-38-9 carbon dioxide 
• 62-53-3 aniline 
• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 79759-11-8 N¹-phenyl-N²-carbethoxy-5-chloro-o.phenylenediamine 
• 201230-82-2 carbon monoxide 
• 25781-92-4 5-chloro-2-nitro-N-phenylaniline 

Downstream Products

• 79759-32-3 5-Chloro-1-ethyl-3-phenyl-1,3-dihydro-benzoimidazol-2-one 
• 79759-33-4 5-Chloro-3-phenyl-1-propyl-1,3-dihydro-benzoimidazol-2-one 
• 79759-91-4 2-oxo-3-phenyl-5-chloro-benzimidazolin-1-acetonitrile 
• 79759-92-5 1-aminoethyl-3-phenyl-5-chloro-benzimidazolin-2-one 
• 79759-56-1 1-phthalimidoethyl-3-phenyl-5-chloro-benzimidazolin-2-one 
• 79759-54-9 2-oxo-3-phenyl-5-chloro-benzimidazolin-1-yl-thioacetamide 
• 79759-53-8 2-oxo-3-phenyl-5-chloro-benzimidazolin-1-yl-acetic acid 
• 79759-55-0 1-chloroethyl-3-phenyl-5-chloro-benzimidazolin-2-one 
• 79759-87-8 5-Chloro-1-methyl-3-phenyl-1,3-dihydro-benzoimidazole-2-thione 
• 79759-36-7 (5-Chloro-2-oxo-3-phenyl-2,3-dihydro-benzoimidazol-1-yl)-acetic acid ethyl ester 
• 37385-92-5 5-chloro-1-methyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 79759-38-9 5-Chloro-1-(2-hydroxy-ethyl)-3-phenyl-1,3-dihydro-benzoimidazol-2-one 
• 79759-41-4 5-Chloro-3-phenyl-1-prop-2-ynyl-1,3-dihydro-benzoimidazol-2-one 
• 79759-40-3 1-benzyl-5-chloro-3-phenyl-1,3-dihydro-benzoimidazol-2-one 

Relevant academic research and scientific papers

Aryliminophosphoranes as Key Intermediates in the One-Pot Synthesis of 1-Aryl-1,3-dihydro-2H-benzimidazol-2-ones from N-Aryl-2-nitrosoanilines and Carbon Dioxide under Mild Metal-Free Conditions

A new and convenient protocol is presented for the synthesis of 1-arylbenzimidazol-2-ones by a one-pot reaction of N-aryl-2-nitrosoanilines using solid carbon dioxide as a source of the key carbonyl moiety. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The atom economy of the synthesis of the starting nitrosoanilines, accomplished by substitution of hydrogen, makes the entire synthesis of the target compounds environmentally friendly.

Role of Alkali Halides in the Synthesis of Nitrogen Containing Heterocycles by Reductive Carbonylation of Aromatic Nitro-Derivatives Catalysed by Ru3(CO)12

The presence of alkali halides as co-catalysts in the reductive carbonylation of o-nitrobiphenyl 1 catalysed by Ru3(CO)12 strongly increases the rate of reactions and slectivity towards heterocyclization products .With sodium halides, depending on the anion, the selectivity for carbazole is in the order Cl- > Br- ca.F- I-; whereas the selectivity for 5H-phenanthridin-6-one is the reverse I- > Br- ca.F- > Cl-.The influence of the cation can be explained with the polarization of a CO ligand of the ruthenium cluster, due to the interaction of the alkali cation with the oxygen lone pair.In fact high yields (>80percent) of heterocyclization products are obtained when the alkali cation is free to coordinate the CO.When this interaction is reduced, by sequestering the cation with crown-ethers, or better with cryptands, the yield of heterocyclic products is 14percent and 0percent respectively.The role of the anion and cation in the catalytic mechanism are discussed.The attempted extension of this reaction to other nitro-derivatives for the potential synthesis of aromatic heterocycles with larger rings are also reported.