22316-55-8

Basic information

• Product Name: 8-chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
• Synonyms: 7-Chloro-5-phenyl-1,5-dihydro-3H-1,5-benzodiazepine-2,4-dione;8-chloro-1-phenyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione;8-chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione;7-Chloro-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione;Desmethylclobazam;Norclobazam;1H-1,5-Benzodiazepine-2,4(3H,5H)-dione, 8-chloro-1-phenyl-;Clofazin
• CAS NO: 22316-55-8
• Molecular Formula: C₁₅H₁₁ClN₂O₂
• Molecular Weight: 286.71304
• EINECS: 244-909-2
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 22316-55-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: >239°C (dec.)
• Boiling Point: 601.8 °C at 760 mmHg
• Flash Point: 2℃
• Appearance: /
• Density: 1.363 g/cm³
• Vapor Pressure: 1.95E-14mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: Controlled Substance, -20?C Freezer
• PKA: 7.57±0.20(Predicted)
• CAS DataBase Reference: 8-chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 8-chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione(22316-55-8)
• EPA Substance Registry System: 8-chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione(22316-55-8)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 2
• Hazardous Substances Data: 22316-55-8(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 22316-55-8 differently. You can refer to the following data:
1. N-Desmethylclobazam (Item No. 18564) is an analytical reference material that is structurally categorized as a benzodiazepine. It is a major active metabolite of clobazam, produced primarily by the action of cytochrome P450 isoform 3A4. N-Desmethylclobazam positively modulates GABAA receptors (EC50s range from 98 to 151 μM, depending on subunit configuration). This product is intended for research and forensic applications.
2. N-Desmethylclobazam (CRM) (Item No. 18888) is a certified reference material that is structurally categorized as a benzodiazepine. It is a major active metabolite of clobazam, produced primarily by the action of cytochrome P450 isoform 3A4. N-Desmethylclobazam (CRM) positively modulates GABAA receptors (EC50s range from 98 to 151 μM, depending on subunit configuration). This product is intended for research and forensic applications.

Chemical Properties

Off-White Solid

Uses

The major metabolite of Clobazam Controlled substance (depressant).

General Description

A Certified Solution Standard for use in LC or GC applications from forensic and forensic toxicology analysis to urine drug testing. N-Desmethylclobazam, found in urine, serum, and plasma, is the pharmacologically active, major metabolite of clobazam.

InChI:InChI=1/C15H11ClN2O2/c16-10-6-7-12-13(8-10)18(11-4-2-1-3-5-11)15(20)9-14(19)17-12/h1-8H,9H2,(H,17,19)

Upstream product

• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 105-53-3 diethyl malonate 
• 16695-14-0 Malonic acid monomethyl ester 
• 610-40-2 3,4-dinitro-chlorobenzene 
• 700-37-8 4-chloro-2-fluoro-nitrobenzene 
• 1663-67-8 malonoyl dichloride 
• 62-53-3 aniline 
• 89-63-4 4-Chloro-2-nitroaniline 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 603-33-8 triphenylbismuthane 
• 61911-86-2 7-chloro-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 
• 22316-45-6 ethyl 2-(N-(5-chloro-2-nitrophenyl)-N-phenylamino)formylacetate 
• 25781-92-4 5-chloro-2-nitro-N-phenylaniline 
• 22316-46-7 N-carbethoxy acetyl N-phenyl 5-chloro o-phenylene diamine 

Downstream Products

• 54705-80-5 8-chloro-6-phenyl-4H-<1,24>triazolo<4,3-a><1,5>benzodiazepin-5(6H)-one 
• 54748-06-0 8-chloro-1-methyl-6-phenyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepin-5(6H)-one 
• 153901-40-7 6-phenyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine-5(6H)-thione 
• 153901-44-1 8-Chloro-5-methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 
• 153901-41-8 8-chloro-1-methyl-6-phenyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine-5(6H)-thione 
• 153901-45-2 8-Chloro-1-methyl-5-methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 
• 153901-51-0 (8-Chloro-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-yl)-dimethyl-amine 
• 153901-38-3 8-chloro-1,6-diphenyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepin-5(6H)-one 
• 153901-42-9 8-chloro-1,6-diphenyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine-5(6H)-thione 
• 153901-47-4 [2-(8-Chloro-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-ylsulfanyl)-ethyl]-dimethyl-amine 
• 153901-52-1 8-Chloro-5-morpholin-4-yl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 
• 153901-46-3 8-Chloro-5-methylsulfanyl-1,6-diphenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 
• 153901-57-6 (8-Chloro-1,6-diphenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-yl)-dimethyl-amine 
• 153901-55-4 8-Chloro-1-methyl-5-morpholin-4-yl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 

Relevant articles and documents

Method for industrially producing clobazam

The invention discloses a method for industrially producing clobazam, and belongs to the technical field of medicine synthesis. According to the method, 5-chloro-2-nitrobenzidine is used as a raw material, and a clobazam bulk drug is prepared through processes of acylation, reduction ring closing, methylation and refining. According to the invention, the problems that reagents with high toxicity are used in the prior art, the pollution is serious, and potential safety hazards exist in the pressurized hydrogenation reaction are solved, the production cost is reduced, and the product quality and economic benefits are improved.

Method being suitable for industrially producing clobazam

The invention discloses a method of industrially producing clobazam and belongs to the technical field of medicine synthesis. With 5-chloro-2-nitrobenzidine as an initial raw material, the method includes the steps of reduction with a nano heavy metal granular catalyst, catalytic condensation with Lewis acid, methylation, and purification to prepare the clobazam that satisfies clinical medicinal requirement. The method solves the problems of heavy toxicity and serious pollution in the prior art, is beneficial to labor protection and reduces production cost, and improves product quality and economic benefit.

AN IMPROVED PROCESS FOR THE PREPARATION OF CLOBAZAM AND ITS INTERMEDIATE

The present invention provides an improved process for the preparation of 8-chloro-1-phenyl- 1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (hereafter referred to as the compound (IV)), which is useful as a key intermediate for the synthesis of Clobazam (referred to as the compound (I)) 7-chloro-1-methyl-5-phenyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione. The process of the present invention further involves transformation of the compound (IV) into Clobazam (I), comprising (a) reacting the compound (II) (as described herein) with monoalkyl malonate in the presence of a coupling agent to obtain the compound (III) (as described herein); followed by the cyclization using a base; (b) reacting the compound-IV (as described herein) obtained from step (a) with methylating agent. The process of the present invention involves formation of novel intermediates methyl 3-((4- chloro-2-(phenylamino)phenyl)amino)-3-oxopropanoate (IlIa) and 3-((4-chloro-2- (phenylamino)phenyl)amino)-3-oxopropanoic acid (V).