37385-92-5

Basic information

• Product Name: 1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one
• Synonyms: 1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one
• CAS NO: 37385-92-5
• Molecular Formula: C₁₄H₁₁ClN₂O
• Molecular Weight: 258.7
• Mol File: 37385-92-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 152-153 °C(Solv: ethanol (64-17-5))
• Boiling Point: 404.6°Cat760mmHg
• Flash Point: 198.5°C
• Appearance: /
• Density: 1.338g/cm³
• Vapor Pressure: 9.36E-07mmHg at 25°C
• Refractive Index: 1.65
• PKA: -0.02±0.20(Predicted)
• CAS DataBase Reference: 1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one(37385-92-5)
• EPA Substance Registry System: 1,3-Dihydro-5-chloro-1-methyl-3-phenyl-2H-benzimidazol-2-one(37385-92-5)

Safety Data

• Hazardous Substances Data: 37385-92-5(Hazardous Substances Data)

Usage

Uses

5-Chloro-1,3-dihydro-1-methyl-3-phenyl-2H-benzimidazol-2-one is an intermediate in the synthesis of Clobazam (C582500), a benzodiazepine psychotherapeutic agent and anxiolytic agent.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.

Compounds with antiulcer and antisecretory activity. I. 3-Aryl-benzimidazolin-2-ones and -thiones

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