23751-99-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(5-chloro-2-(dimethylamino)phenyl)(phenyl)methanone is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Production:
In the agrochemical industry, (5-chloro-2-(dimethylamino)phenyl)(phenyl)methanone is utilized as an intermediate in the creation of compounds that can be used for pest and disease control in agriculture, aiming to improve crop yields and protect plants from harmful organisms.
Used in Pharmacological Research:
(5-chloro-2-(dimethylamino)phenyl)(phenyl)methanone is also used in pharmacological research as a subject of study for its potential anti-inflammatory and antimicrobial properties, which could lead to the development of new treatments for various medical conditions.

Upstream product

• 1022-13-5 5-chloro-2-(methylamino)benzophenone 
• 50-00-0 formaldehyd 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 439-14-5 diazepam 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 146470-01-1 C₁₆H₁₈ClN₅*ClH 

Relevant academic research and scientific papers

Acid hydrolysis of diazepam. Kinetic study of the reactions of 2-(N- methylamino)-5-chlorobenzophenone, with HCl in MeOH-H2O

In the acid hydrolysis of diazepam (1), several unusual products, apart from 2-(N-methylamino)-5-chlorobenzophenone (2) and glycine, were isolated. On the assumption that some of those products could arise from further degradation of 2, the reaction of this compound with 0.5-2 M HCl was studied, in 1:1 MeOH-H2O, at 60 and 80 °C. Several unexpected products were isolated from the reaction of 2 with HCl, namely, 2-amino-5-chlorobenzophenone (3), 2- (N,N-dimethylamino)-5-chlorobenzophenone (4), 2-(N-methylamino)-3,5- dichlorobenzophenone (5), 2-amino-3,5-dichlorobenzophenone (6), 2,4-dichloro- 10-methyl-9,10-acridinone (7), and 2,4-dichioro-9,10-acridinone (8). The methyl transfers, the chlorination, and the cyclization reactions that give rise to products 3-8 are unexpected under the present reaction conditions. The rate of reaction of 2, as well as the rate of formation of compounds 3- 6, was measured at several HCl concentrations.

Asymmetric synthesis of 1,3-diamines by diastereoselective reduction of enantiopure n-tert-butanesulfinylketimines: unusual directing effects of the ortho-substituent

(Figure Presented) Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert- butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.

Kinetic and mechanistic studies on the hydrolysis and photodegradation of diazepam and alprazolam

The corresponding o-aminobenzophenones are usually reported as the main degradation products in the hydrolysis of 1,4-benzodiazepinones. Nevertheless, in previous studies of diazepam (DZ) in acidic aqueous medium we isolated and characterized seven unexpected degradation products. Kinetic measurements under several reaction conditions shed some light on the mechanisms of the complex reactions that are taking place, and photochemical studies give hints on the mechanisms of chlorination and annelation processes. Alprazolam (AL) seems to exhibit an unusually high stability against hydrolysis under several conditions; nevertheless, the structure is sensitive to photolytic cleavage. The photodegradation of AL was studied in aqueous and methanolic solutions. Characterization of the isolated products by 1H and 13C NMR and mass spectrometry revealed that electron transfer, oxidation and rearrangement reactions take place. The influence of several variables such as pH, solvent composition and light irradiation were examined and mechanisms for the formation of three photoproducts are proposed. A specific method for the determination of AL in the presence of photoproducts was developed, which allowed kinetic determinations of the photostability of AL. The photosensitivity observed in some patients treated with AL seems to be due to one of the characterized photoproducts. Copyright

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.

Kinetic Study of the Reactions of 2-Amino-5-chlorobenzophenone with HCl in MeOH-H2O

The reaction of 2-amino-5-chlorobenzophenone (1) with 0.5-2 M HCl was studied in 1:1 (v/v) MeOH-H2O at 60 and 80 deg C.Products that were isolated were characterized as 2-(N-methylamino)-5-chlorobenzophenone (2), 2-amino-3,5-dichlorobenzophenone (3), 2-N-methylamino-3,5-dichlorobenzophenone (4), 2-(N,N-dimethylamino)-5-chlorobenzophenone (5), 2,4-dichloro-10-methyl-9,10-acridinone (6) and 2,4-dichloro-9,10-acridinone (7).The rates of reaction of 1 and the rates of formation of 2-5 were measured at several HCl concentrations.The methyl transfers, the chlorination and the cyclization reactions that give rise to 2-7 were unexpected under the present reaction conditions.A set of differential equations was proposed in order to calculate the rate constants for each step of this complex reaction.The proposed reaction scheme also takes into account the reaction 21 and permits the calculation of the rate constants for this reversible reaction.The experimental values of the rate constants for reaction of 1 were compared with those for 2 under the same reaction conditions, in order to evaluate the importance of the methyl group on the methyl transfer reactions; it was found that the methyl group is not required for the unexpected reaction to occur. - Keywords: 2-amino-5-chlorobenzophenone; hydrochloric acid; kinetics

Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones

LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six α-aminophenones 4-9 into the corresponding optically active β-aminoalcohols 10-15 whose ee's were in the range of 40-97% after chroma