Efficient acetylation of primary amines and amino acids in environmentally benign brine solution using acetyl chloride

Abstract

Acetyl chloride is one of the most commonly available and cheap acylating agent but its high reactivity and concomitant instability in water precludes its use to carry out acetylation in aqueous medium. The present methodology illustrates the efficient acetylation of primary amines and amino acids in brine solution by means of acetyl chloride under weakly basic condition in the presence of sodium acetate and/or triethyl amine followed by trituration with aqueous saturated bicarbonate solution. This effort represents the first efficient use of this most reactive but cheap acetylating agent to acetylate amines in excellent yields in aqueous medium. This is a potentially useful green chemical transformation where reaction takes place in environment-friendly brine solution leading to easy work-up and isolation of the amide derivatives. Mechanistic rationale of this methodology is also important.

Thioester-Based Latent Curing Agent for Thermally Conductive Epoxy Composites

“…There are various methods to protect the thiol functional group, including the incorporation of tert -butyl groups or acyl groups. ,, In our research, we embarked on synthesizing a thioester using acetyl chloride and triethylamine under mild reaction conditions, aiming for high yield and scalability (Figure a). , The core structure and physical properties of thioesters derived from this facile acylation reaction can vary depending on the type of thiols used. We selected a commercial multifunctional thiol, pentaerythritol tetrakis(3-mercaptopropionate) (PETMP), to establish a 3D cross-linked network.…”

Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol

“…The effective development of brine-mediated benzoylation [32] as well as acetylation [33] of amines in our laboratory motivated us to carry out this benzoylation in the presence of sodium chloride in the solid phase. The presence of solid sodium chloride made the solid mass porous, for which the isolation of the benzoates became easier, and this also led to better yield as tabulated in Table 1.…”

A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system

“…To improve and develop the applicability of the present method, synthesis of α-amino acid amides, were examined by using PPh 3 / NCBT / amines system. At first, N-acetylated α-amino acids were prepared by the method reported previously, 52 to prevent any interference of amino groups.…”