N-chloroacetylation of amines
- Publication: Green Chemistry Letters and Reviews, (2018), (11), 552-558
- Patent: Balaji B.S, Neha Dalal. Efficient and selective N-haloacylation of amines. Indian Patent, 354900, 2020
For the first time, we have developed a 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 protocol 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.
N-chloroacetylation of aminoalcohols
- Publication: Green Chemistry Letters and Reviews, (2018), (11), 534-543
- Patent: Balaji B. S, Neha Dalal. Efficient and selective N-haloacylation of amino alcohols. Indian Patent application, 201711040249
We have developed an efficient and highly chemoselective N-chloroacetylation of amino compounds (amino alcohols, amino acids) by chloroacetyl chloride, without compromising its high reactivity, to give chloroacetamides in phosphate buffer within 20 min. Through intermolecular competitive reactions we have shown that anilines and aliphatic amines can be selectively N-chloroacylated in the presence of alcohols and phenols. The acylated products are obtained in high yields and can be easily isolated without chromatographic separation. This reaction represents the first example of a metal-free biocompatible synthesis under neutral conditions. This method is eco-friendly, easily scalable and robust. We have further studied the intramolecular competitive reactions of aminoalcohols and prepared various N-chloroacetamides in very good yields. We have extended this protocol to ceramides synthesis as well.