2556-46-9

Usage

Preparation

To a three-necked, round-bottomed flask equipped with a mechanical stirrer, dropping funnel, and condenser is added 90.0 gm (0.46 mole) of pure dry benzanilide (see Note a) and 95 gm (0.46 mole) of phosphorus pentachloride (see Note b). The mixture is stirred to reduce the lumps and then heated for ? hr at 110°C and 1?hr at 160°C, or until the evolution of hydrogen chloride ceases. Then 36.4 gm (0.46 mole) of KOH-dried pyridine (see Note c) is added with stirring, followed by 42.4 gm (0.46 mole) of freshly distilled aniline. The reaction mixture is heated at 160°C for about 20 min to discharge the red color, cooled to about 90°C, and 250 ml of water is added dropwise to precipitate the product in granular form. The product is filtered and added to 500 ml of 28% aqueous ammonia. The mixture is stirred while gently warming for 1 hr, filtered, dried, and recrystallized from 80% ethanol (8-10 ml/gm product) to afford 73-80% product, m.p. 144-145°C.

Upstream product

• 110-86-1 pyridine 
• 93-98-1 N-phenyl benzoyl amide 
• 98-09-9 benzenesulfonyl chloride 
• 142-04-1 aniline hydrochloride 
• 74225-48-2 α-(p-diethylaminophenyl)iminophenylacetonitrile 
• 98-88-4 benzoyl chloride 
• 102-07-8 bis(diphenyl)urea 
• 103-71-9 phenyl isocyanate 
• 543-20-4 succinoyl dichloride 
• 98-07-7 Benzotrichlorid 
• 62-53-3 aniline 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 6921-34-2 benzylmagnesium chloride 
• 108-95-2 phenol 

Downstream Products

• 102466-87-5 3-(α-phenylimino-benzyl)-3H-benzofuran-2-one 
• 14606-38-3 bis-(α-phenyliminobenzyl) sulfide 
• 1527-91-9 N-phenylbenzamidine 
• 56722-36-2 N-(4-chloro-phenyl)-N'-phenyl-benzamidine 
• 55352-47-1 4-(anilino-phenyl-methylene)-3-phenyl-4H-isoxazol-5-one 
• 61505-49-5 C₂₄H₂₀N₂O₃ 
• 33821-84-0 3,6-Dihydro-6-oxo-1,2,3-triphenyl-1-pyrimidinium-4-olat 
• 61201-43-2 3,6-Dihydro-5-methyl-6-oxo-1,2,3-triphenyl-1-pyrimidinium-4-olat 
• 610-43-5 N-Benzyl-N-phenyl-carbamidsaeureethylester 
• 940866-95-5 ethyl N-phenyl-α-phenylglycinate 
• 56409-80-4 5-benzyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate 
• 61201-41-0 5-ethyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate 
• 87222-99-9 5-butyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate 
• 223565-36-4 4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites

A selective mono-N-arylation strategy of amidines under Chan-Lam conditions is described. During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan-Lam mono-N-arylation. The scope of the process is demonstrated, and then applied to access the first mono-N-arylated analogues of pentamidine. Sub-micromolar activity against kinetoplastid parasites was observed for several analogues with no cross-resistance in pentamidine and diminazene-resistant trypanosome strains and against Leishmania mexicana. A fluorescent mono-N-arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono-N-arylated pentamidine series was confirmed by UV-melt measurements using AT-rich DNA. This work highlights the potential to use Chan-Lam mono-N-arylation to develop therapeutic leads against diamidine-resistant trypanosomiasis and leishmaniasis.

A Convenient Synthesis of Amidines via Cycloaddition-Decarboxylation of Isocyanates and Nitrones

A base-promoted reaction between isocyanates and nitrones has been described, allowing an access to a variety of important functionalized amidines under mild reaction conditions. This strategy provides a convenient, effective, and scalable approach for the direct assembly of amidine compounds from simple starting materials in excellent yields.

Access to Amidines and Arylbenzimidazoles: Zinc-Promoted Rearrangement of Oxime Acetates

An efficient and straightforward zinc-promoted rearrangement of oxime acetates with arylamines for the synthesis of amidines has been developed under mild conditions. This process involves N?O/C?C bond cleavages and C?C/C?N bond formations. Various oxime

Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines

A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

Diverse tandem cyclization reactions of o -cyanoanilines and diaryliodonium salts with copper catalyst for the construction of quinazolinimine and acridine scaffolds

Two cyclization modes are realized to produce different nitrogen-containing heterocycles, i.e.; quinazolin-4(3H)-imines and acridines by assembling o-cyanoanilines and diaryliodonium salts via tandem reaction pathways.

Highly active nano-MgO catalyzed, mild, and efficient synthesis of amidines via electrophilic activation of amides

Nano-MgO catalyzed synthesis of amidine derivatives is developed under solvent-free reaction condition at 70 C. Reusability of the catalyst and shorter reaction time as well as high yields are the advantages of this procedure.

Nitrenic reactivity of diazirines

Butyl 3-bromo-3H-diazirine-3-carboxylate (7) and 3-bromo-3-phenyl-3H- diazirine (17) exhibit nitrenic reactivity with phenylmagnesium bromide or tetrabutylammonium cyanide. The formation of several N,N′-disubstituted amidines is attributed to the intermediacy of 1-phenyl or 1-cyano-1H-diazirines possessing a singlet imidoylnitrene character at the N2 atom. Most notably, the reaction of 7 with PhMgBr in diethyl ether affords 2-hydroxy-2,2,N- triphenylacetamidine (9) and 2-methyl-5,5-diphenyl-4-phenylamino-2,5- dihydrooxazole (10) as products derived from nitrene insertion to the ether α-C-H bond.

High temperature vapor phase reactions of nitrogen trifluoride with benzylic substrates

At temperatures around 400°C, nitrogen trifluoride (NF3) readily reacts with benzylic substrates. Products vary with the substrate, but are all the result of difluoroamination at the benzylic position. Toluene and ethylbenzene produce benzonitrile. Cumene produces α-methylstyrene. Diphenylmethane produces benzanilide. Little or no direct fluorination or radical dimerization is observed.

Efficient access to polysubstituted amidines, benzimidazoles and pyrimidines from amides

Polysubstituted amidines, benzimidazoles and pyrimidines were synthesized via the electrophilic activation of amides with trifluoromethanesulfonic anhydride and 2-chloropyridine. The one-pot protocol is concise and efficient and the substrates are readily available.

Extraction-spectrophotometric determination of rhenium(VII) with thiocyanate and amidines in the presence of cetyltrimethylammonium bromide

A simple and selective spectrophotometric method has been developed for the determination of rhenium(VII) in the ore sample based on the reaction of ReVII with thiocyanate in the presence of tin(II) chloride in sulfuric acid media and subsequent extraction of the complex with chloroform solution of N,N′-diphenylbenzamidine (DPBA) and its nine derivatives in the presence of a cationic surfactant, cetyltrimethylammonium bromide (CTAB). The effects of acids and organic solvents on the extraction of the metal and colour intensity of the complex are discussed. The tolerance limits of diverse ions are very high. MoVI interferes it but is removed by prior precipitation by oxine effectively. The molar absorptivity and detection limit of the method with DPBA are (3.65 ± 0.02) × 104 dm -3 mol-1 cm-1 and 0.004 μg ml-1, respectively. The relative standard deviation of the method at a level of 25 μg ReVII / 10 ml is ± 1.2%.