37385-92-5

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one is used as an intermediate in the synthesis of Clobazam (C582500), a benzodiazepine psychotherapeutic agent and anxiolytic agent. Clobazam is widely prescribed for the treatment of anxiety, panic disorders, and certain seizure disorders due to its effectiveness in modulating the GABA receptor, leading to a calming effect on the central nervous system.
1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one's role in the synthesis of Clobazam highlights its importance in the development of medications that address a range of neurological and psychiatric conditions. Its unique chemical structure allows for the creation of therapeutic agents with specific properties, making it a valuable component in the pharmaceutical industry's efforts to develop new and improved treatments for various health issues.

InChI:InChI=1/C14H11ClN2O/c1-16-12-8-7-10(15)9-13(12)17(14(16)18)11-5-3-2-4-6-11/h2-9H,1H3

Upstream product

• 54986-47-9 6-chloro-1,3-dihydro-1-phenyl-2H-benzimidazol-2-one 
• 77-78-1 dimethyl sulfate 
• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 79759-11-8 N¹-phenyl-N²-carbethoxy-5-chloro-o.phenylenediamine 
• 932-96-7 N-methyl(p-chloroaniline) 
• 103-71-9 phenyl isocyanate 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 
• 106-47-8 4-chloro-aniline 
• 59681-66-2 4-chloro-1-N-methylbenzene-1,2-diamine 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 15965-71-6 5-chloro-1,3-dihydro-1-methyl-2H-benzimidazol-2-one 
• 17878-37-4 1-bromo-2-(trimethylsilyl)benzene 
• 95-56-7 2-hydroxybromobenzene 
• 86504-25-8 N-(4-chloro-phenyl)-N-methyl-N'-phenyl-urea 

Downstream Products

• 79759-87-8 5-Chloro-1-methyl-3-phenyl-1,3-dihydro-benzoimidazole-2-thione 

Relevant academic research and scientific papers

Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones

There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.

A benzo oxazolone and benzimidazolone of N - aryl compound into method (by machine translation)

The invention relates to a benzo oxazolone and benzimidazolone of N - aryl compound into a method, involving the two kind of compound preparation, in order to 2 - resolution method oxazolones or 1 - methyl - 2 - benzimidazolone, and cesium fluoridebenzyne

Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates

A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.

Metal-Free Oxidative C-H Amidation of N,N′-Diarylureas with PhI(OAc)2: Synthesis of Benzimidazol-2-one Derivatives

Benzimidazol-2-ones have various biological functions and are usually prepared by reactions of substituted benzene-1,2-diamines with carbonyl-containing compounds or intramolecular N-arylations using substrates with carbon-halogen bonds. However, the star