5606-40-6

Basic information

• Product Name: 2-(methylamino)-5-chlorobenzophenone imine
• Synonyms: 2-(methylamino)-5-chlorobenzophenone imine
• CAS NO: 5606-40-6
• Molecular Formula: C₁₄H₁₃ClN₂
• Molecular Weight: 244.72
• Mol File: 5606-40-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 396.7°C at 760 mmHg
• Flash Point: 193.7°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 1.68E-06mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 2-(methylamino)-5-chlorobenzophenone imine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(methylamino)-5-chlorobenzophenone imine(5606-40-6)
• EPA Substance Registry System: 2-(methylamino)-5-chlorobenzophenone imine(5606-40-6)

Safety Data

• Hazardous Substances Data: 5606-40-6(Hazardous Substances Data)

Usage

Description

2-(Methylamino)-5-chlorobenzophenone imine, also known as 4-Chloro-2-(iminophenylmethyl)-N-methylbenzenamine, is an organic compound with a chemical structure that features a benzene ring with a methylamino group at the 2nd position, a chlorine atom at the 5th position, and an imine functional group. It is an impurity found in Diazepam, a pharmaceutical drug.

Uses

Used in Pharmaceutical Industry:
2-(Methylamino)-5-chlorobenzophenone imine is used as an impurity in the production of Diazepam (D416855) for its anxiolytic, muscle relaxant, and anticonvulsant properties. It plays a role in the overall effectiveness of Diazepam, which is utilized in the treatment of anxiety, muscle spasms, and seizures.
As an impurity, it is essential to monitor and control the levels of 2-(methylamino)-5-chlorobenzophenone imine in Diazepam to ensure the safety and efficacy of the drug. The presence of this impurity may affect the drug's pharmacological activity, and therefore, its quality control is crucial in the pharmaceutical manufacturing process.

InChI:InChI=1/C14H13ClN2/c1-17-13-8-7-11(15)9-12(13)14(16)10-5-3-2-4-6-10/h2-9,16-17H,1H3/b16-14+

Upstream product

• 719-59-5 5-chloro-2-aminobenzophenone 
• 74-88-4 methyl iodide 
• 52395-00-3 N-methyl-N-(2-benzoyl-4-chlorophenyl)formamide 
• 10352-28-0 N-(2-benzoyl-4-chlorophenyl)formamide 

Downstream Products

• 84593-91-9 7-Chloro-1-methyl-2,3-bis-(4-methyl-piperazin-1-yl)-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepine 
• 84505-10-2 7-Chloro-1-methyl-5-phenyl-2,3-di-piperidin-1-yl-2,3-dihydro-1H-benzo[e][1,4]diazepine 
• 84505-09-9 7-Chloro-1-methyl-2,3-di-morpholin-4-yl-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepine 
• 26313-37-1 5-chloro-2-(N-methyl-trichloroacetamido)benzophenone 
• 80170-86-1 6-chloro-3,4-dihydro-1-methyl-4-phenyl-4-trichloromethyl-2(1H)-quinazolinone 
• 20927-53-1 6-chloro-1-methyl-4-phenyl-2(1H)-quinazolinone 
• 70395-32-3 6-chloro-2-chlorofluoromethyl-1,2-dihydro-2-hydroxy-1-methyl-4-phenylquinazoline 
• 60628-55-9 3-fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one 

Relevant articles and documents

Mechanism of Alkaline Hydrolysis of Diazepam

Diazepam (1) is a frequently prescribed hypnotic/anxiolytic drug in worldwide use. Compound 1 is hydrolyzed in alkaline medium to form 2-methylamino-5-chlorobenzophenone imine (2) and 2-methylamino-5-chlorobenzophenone (3); the ratio of 2:3 increases with increasing NaOH concentration (J. Pharm. Sci. 85, 745-748, 1996). The mechanism in the conversion of 1 to 2 and 3 via various intermediates is the subject of this report. Results of hydrolysis kinetics and structural identification of some intermediate products indicated an initial hydroxide attack at the C2-carbonyl carbon of 1, resulting in the formation of a dioxide (7, 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2,2-dioxide). Compound 7 was characterized by proton NMR spectroscopy and via its monomethyl ether (8, 7-chloro-1,3-dihydro-2-hydroxy-2-methoxy-1-methyl-5-phenyl-2H-1,4-benzodiazepme) . The seven-member diazepine ring of 7 opened at the N1-C2 bond to form aglycinate [5, 2-methylamino-5-chloro-α-(phenylbenzylidene)glycinate]. Compound 7 (and/or 5) underwent an additional hydroxide attack at the C5-N4 imine bond to form a tetrahedral intermediate, which decomposed to form 2 and 3.

Intermediates for preparing 1,4-benzodiazepine-2-ones having a carboxylic acid ester or amide group in the 3-position

Intermediates for preparing novel benzodiazepines having the formula SPC1 In which R1 is a hydrogen or halogen atom or a trifluoromethyl, loweralkyl, loweralkoxy, nitro or amino group; R2 is a furyl, a thienyl, cyclohexyl, a loweralkyl group or a phenyl group which may be substituted by a halogen atom or by a trifluoromethyl, nitro, loweralkoxy or loweralkyl group; and R3 is a hydrogen atom or a loweralkyl group; and R4 is lowercarbalkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-diloweralkylcarbamoyl, N-(diloweralkylaminoalkyl)carbamoyl, a group having the formula --COOCat in which Cat is a cation of an alkali metal or a semication of an alkaline earth metal or COOCat.CatOH, said intermediates being ortho-aminoaryl ketimines having the formula SPC2 Wherein R is hydrogen or EQU1 R1, R2, and R3 are as defined above, R4 is a hydrogen atom, a lowercarbalkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-diloweralkylcarbamoyl, N-(diloweralkylaminoalkyl)-carbamoyl, alkyl or substituted alkyl group; and R5 is a loweralkyl group.