38674-90-7

Upstream product

• 108-24-7 acetic anhydride 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 2735-73-1 1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 62-53-3 aniline 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 98-95-3 nitrobenzene 
• 60544-72-1 [1,4]benzoquinone-mono-[phenyl-(4-phenylazo-phenyl)-hydrazone] 
• 64-19-7 acetic acid 

Downstream Products

• 22952-14-3 1,2-bis(p-tolylsulfonyl)ethane 
• 102656-40-6 acetic acid-(4-{N-[2-(toluene-4-sulfonyl)-ethyl]-anilino}-anilide) 
• 265324-03-6 N-(4-acetylaminophenyl)-N'-(4-aminophenyl)-1,4-phenylenediamine 

Relevant academic research and scientific papers

One drop chemical derivatization - DESI-MS analysis for metabolite structure identification

Structural elucidation of metabolites is an important part during the discovery and development process of new pharmaceutical drugs. Liquid Chromatography (LC) in combination with Mass Spectrometry (MS) is usually the technique of choice for structural identification but cannot always provide precise structural identification of the studied metabolite (e.g. site of hydroxylation and site of glucuronidation). In order to identify those metabolites, different approaches are used combined with MS data including nuclear magnetic resonance, hydrogen/deuterium exchange and chemical derivatization followed by LC-MS. Those techniques are often time-consuming and/or require extra sample pre-treatment. In this paper, a fast and easy to set up tool using desorption electrospray ionization-MS for metabolite identification is presented. In the developed method, analytes in solution are simply dried on a glass plate with printed Teflon spots and then a single drop of derivatization mixture is added. Once the spot is dried, the derivatized compound is analyzed. Six classic chemical derivatizations were adjusted to work as a one drop reaction and applied on a list of compounds with relevant functional groups. Subsequently, two successive reactions on a single spot of amoxicillin were tested and the methodology described was successfully applied on an in vitro incubated alprazolam metabolite. All reactions and analyses were performed within an hour and gave useful structural information by derivatizing functional groups, making the method a time-saving and efficient tool for metabolite identification if used in addition or in some cases as an alternative to common methods.

Pd-catalyzed synthesis of aryl amines via oxidative aromatization of cyclic ketones and amines with molecular oxygen

Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of amines with nonaromatic ketones. Under optimized reaction conditions, primary and secondary amines are selectively arylated in good yields with cyclohexanones and 2-cyclohexen-1-ones in the presence of a Pd-catalyst under an atmosphere of molecular oxygen.

Palladium-catalyzed one-pot diarylamine formation from nitroarenes and cyclohexanones

The first palladium-catalyzed diarylamine formation from nitroarenes and cyclohexanone derivatives using borrowed hydrogen is described. Various diarylamines were selectively obtained in good to excellent yields. The reaction tolerated a wide range of functionalities. The nitro reduction, cyclohexanone dehydrogenation, and imine formation and reduction were realized in a cascade without an external reducing reagent and oxidant.

Rational and predictable chemoselective synthesis of oligoamines via Buchwald-Hartwig amination of (hetero)aryl chlorides employing Mor-Dalphos

We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl) morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, α-branched acyclic primary alkylamines, hindered electron-rich primary anilines ? cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, α,α-branched primary alkylamines, and primary amides. The new isomeric ligand N-(4-(di(1-adamantyl)phosphino)phenyl)morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallographically characterized; the [Pd(cinnamyl)Cl]2/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl] 2/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl] 2/L1 and 4-chlorotoluene (affording 5a); the alternative regioisomer (5a′) was obtained when using [Pd(cinnamyl)Cl]2/L2. These observations are in keeping with coordination chemistry studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)] + fragment occurred via the primary amine moiety, affording the crystallographically characterized adduct [(L1)Pd(p-tolyl)(NH2CH 2CH2(4-C6H4NH2)] +OTf- (7) in 72% yield.

1,3-Dihydro-1,3-diacetyl-2H-benzimidazol-2-one: A new versatile and selective acetylating agent

1,3-Dihydro-1,3-diacetyl-2H-benzimidazol-2-one (4, DABI) was proven to be a versatile and selective acetylating agent for amines. Selectivity and reactivity are not only superior than those of other known acetylating agents, but also products could be easily separated with excellent yield.

Diphenylamino and indolyl substituted pyromellitides

This invention relates to 3,7-bis(disubstituted aminophenyl- or indolyl)-3,7-bis(diphenylamino)pyromellitides, 3,5-bis(disubstituted aminophenyl- or indolyl)-3,5-bis(diphenylamino)pyromellitides and mixtures thereof useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2,5-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,4-benzenedicarboxylic acids or 2,4-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,5-benzenedicarboxylic acids and mixtures thereof with diphenylamines.