6289-84-5

Usage

Uses

Used in Pharmaceutical Industry:
2-(acetylamino)ethyl benzoate is used as an intermediate in the synthesis of pharmaceuticals for its sedative and analgesic properties, contributing to the development of medications that can alleviate pain and induce a calming effect.
Used in Flavoring Agent:
In the food industry, 2-(acetylamino)ethyl benzoate is used as a flavoring agent to enhance the taste and aroma of various food products, providing a pleasant sensory experience for consumers.
However, it is crucial to handle this chemical with care, as it can be harmful if ingested, inhaled, or comes into contact with the skin. Proper safety measures should be taken during its production, use, and disposal to minimize potential risks.

InChI:InChI=1/C11H13NO3/c1-9(13)12-7-8-15-11(14)10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,12,13)

Upstream product

• 75-05-8 acetonitrile 
• 939-55-9 2-chloroethyl benzoate 
• 3394-31-8 3-acetyl-2-phenyl-oxazolidine 

Relevant academic research and scientific papers

Mechanistic and Synthetic Implications of the Diol-Ritter Reaction: Unexpected Yet Reversible Pathways in the Regioselective Synthesis of Vicinal-Aminoalcohols

The Ritter reaction of 1,2-diolmonoesters with nitriles to 1-vic-amido-2-esters proceeds through dioxonium and nitrilium cation intermediates. To provide the basis for the reaction mechanism, novel forms of these cations were isolated, characterized, and studied by spectroscopic methods and single crystal X-ray analysis. Ground and transition state energies were determined both experimentally and theoretically. Taken together, these data suggest that the reaction proceeds via rapid formation of the dioxonium cation 9, followed by rate determining yet reversible ring opening by acetonitrile to the corresponding nitrilium cation 10 (computed ΔG∞ = 24.7 kcal at 50 °C). Rapid, irreversible hydration of the latter affords the corresponding vic-acetamido ester. Controlled addition of H2O to the dioxonium cation 9 in acetonitrile-d3 results in near-quantitative production of deuterated acetamido ester 13a. Kinetics of this conversion (9 to 13a) are biphasic, and the slow phase is ascribed to either direct cation 9 attack by acetamide to form cation 16 via O-alkylation or by reversible ether formation. Deuterium labeling studies suggest O-alkylated cation 16 does not directly isomerize to N-alkylated cation 18; instead, it reverts to vic-amidoester 13a via the nitrilium pathway. Preliminary results indicate high regioselectivity for primary amide formation in the diol-Ritter sequence.

Variable C2-symmetric analogues of N-hydroxyphthalimide as enantioselective catalysts for aerobic oxidation: Kinetic resolution of oxazolidines

(Chemical Equation Presented) Fast and selective: The aerobic oxidative ring opening of oxazolidine 1 in the presence of a catalytic amount of the chiral N-hydroxyphthalimide analogue 2 was accompanied by efficient kinetic resolution of the oxazolidine. T