naa a22 4500 510734162 CHVBK 20180411083003.0 cr unu---uuuuu 180411e20130501xx s 000 0 eng 10.1007/s12039-013-0400-3 doi (NATIONALLICENCE)springer-10.1007/s12039-013-0400-3 Efficient acetylation of primary amines and amino acids in environmentally benign brine solution using acetyl chloride [Elektronische Daten] [KAUSHIK BASU, SUCHANDRA CHAKRABORTY, ACHINTYA SARKAR, CHANDAN SAHA] 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. Graphical Abstract Aromatic and aliphatic primary amines and amino acids have been acetylated efficiently in brine solution with acetyl chloride under weakly basic conditions in the presence of sodium acetate and/or triethyl amine. The methodology demonstrates successful use of acetyl chloride as a substitute of acetic anhydride for the purpose of acetylation in aqueous medium. Indian Academy of Sciences, 2013 Amines nationallicence acetyl chloride nationallicence brine nationallicence sodium acetate nationallicence triethyl amine nationallicence BASU KAUSHIK Department of Chemistry, St. Paul's Cathedral Mission College, 700 009, Kolkata, India aut CHAKRABORTY SUCHANDRA Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, 700 073, Kolkata, India aut SARKAR ACHINTYA Department of Chemistry, Presidency College, 700 073, Kolkata, India aut SAHA CHANDAN Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, 700 073, Kolkata, India aut Journal of Chemical Sciences Springer-Verlag 125/3(2013-05-01), 607-613 0974-3626 125:3<607 2013 125 12039 https://doi.org/10.1007/s12039-013-0400-3 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s12039-013-0400-3 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- BASU KAUSHIK Department of Chemistry, St. Paul's Cathedral Mission College, 700 009, Kolkata, India aut NATIONALLICENCE 700 1- CHAKRABORTY SUCHANDRA Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, 700 073, Kolkata, India aut NATIONALLICENCE 700 1- SARKAR ACHINTYA Department of Chemistry, Presidency College, 700 073, Kolkata, India aut NATIONALLICENCE 700 1- SAHA CHANDAN Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, 700 073, Kolkata, India aut NATIONALLICENCE 773 0- Journal of Chemical Sciences Springer-Verlag 125/3(2013-05-01), 607-613 0974-3626 125:3<607 2013 125 12039 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer