26926-35-2

Upstream product

• 1093253-55-4 1-phenylvinyl methanesulfonate 
• 124-63-0 methanesulfonyl chloride 
• 65-85-0 benzoic acid 
• 2386-52-9 silver methanesulfonate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 109684-14-2 ethyl 2-benzoylhydrazinoacetate 
• 64-10-8 phenyl carbamate 
• 103-70-8 Formanilid 
• 93-98-1 N-phenyl benzoyl amide 
• 582-61-6 benzoyl azide 
• 2208-05-1 2-(dimethylamino)ethyl benzoate 
• 93-99-2 benzoic acid phenyl ester 

Relevant academic research and scientific papers

Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement

Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.

AMIDATION METHOD AND ESTERIFICATION METHOD USING SULFONIC ACID HALIDE

PROBLEM TO BE SOLVED: To provide a safe and economical method for rapidly synthesizing amides and esters in high yield. SOLUTION: There is provided a method for amidating an amine or a derivative thereof using a sulfonic acid halide, where a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an amine or a derivative thereof as a nucleophile to amidate the amine or the derivative thereof to obtain a corresponding amide or a derivative thereof. In a similar manner, a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an alcohol or a derivative thereof as a nucleophile to esterify the alcohol or the derivative thereof to obtain a corresponding ester or a derivative thereof. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPO&INPIT

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2

A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product. (Chemical Equation).

Carboxylic sulfonic mixed anhydrides: General utility and application to the synthesis of ceftazidime

A high-yielding acylation process which utilizes a mixed anhydride of the type RCO2SO2CH3 for the synthesis of the cephalosporin ceftazidime is detailed. The mixed anhydride is conveniently prepared by addition of methanesulfonyl chloride to the triethylammonium salt of the acid 2a. Although known for some time, these anhydrides have not been used often in acylations. This lack of general utility is explained by side reactions, especially formation of the carboxylic symmetric anhydride in sterically unhindered systems.

Phase-Transfer Catalyzed Synthesis of Amides and Esters of Carboxylic Acids

A convenient one-pot procedure is reported for the preparation of carboxamides and carboxylic acid esters from carboxylic acids and amines or alcohols, respectively.The carboxylic acids are activated by sulfonyl chlorides under solid-liquid phase-transfer conditions using solid potassium carbonate as base and a lipophilic quaternary ammonium salt as catalyst.

Carboxylic Trifluoromethanesulfonic and Methanesulfonic Anhydrides, Synthesis and Dissociation Tendency

Carbonyl chlorides 1 react with silver trifluoromethanesulfonate (2) and silver methanesulfonate (6) to give carboxylic trifluoromethanesulfonic anhydrides 3 and carboxylic methanesulfonic anhydrides 7, resp., in good yields; the anhydrides 3 may be synth