An expedient and rapid green chemical synthesis of N-chloroacetanilides and amides using acid chlorides under metal-free neutral conditions

ABSTRACT

We are reporting for the first time, rapid N-chloroacetylation of anilines and amines in phosphate buffer within 20 min. Primary and secondary amino derivatives (amines, anilines) were efficiently condensed with various acid chlorides (containing aliphatic, aromatic, cyclic and heteroaromatic units). We have also shown that the modification of the electrophilic nature of the substituents on the acid chloride did not affect the product formation and the required amides are formed in high yields. The major advantage of this process is highlighted by the ease of product isolation (simple filtration/precipitation). This process represents the first example of a metal-free, green chemical synthesis under neutral conditions to provide an eco-friendly, easily scalable and robust process for the preparation of amides that expands the scope, utility and applicability of acid chlorides.

GRAPHICAL ABSTRACT

KEYWORDS:

• Acid chlorides
• chloroacetylation
• green chemical method
• phosphate buffer
• herbicides

Acknowledgements

The authors are thankful to AIRF, JNU for NMR and Mass analysis of the samples.

Disclosure statement

The author holds intellectual property rights for this work.

ORCID

B. S. Balaji http://orcid.org/0000-0002-5522-7726

Notes on contributors

B. S. Balaji is an associate professor at School of Biotechnology, Jawaharlal Nehru University. His research interest includes bioorthogonal reactions, anti-cancer research, green chemistry and drug development.

Neha Dalal was a master student at School of Biotechnology, Jawaharlal Nehru University. Currently she is pursuing her Ph.D from Indian Institute of Technology, Bombay.

Additional information

Funding

The authors thank PAC-JNU-DST-PURSE-462 (Phase-II), University with Potential for Excellence (UPE-II)-JNU and DBT- M. Sc. (Biotechnology) program for their support and funding.