A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2

Abstract

Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides.

Synthesis of Water-Soluble Chiral DOTA Lanthanide Complexes with Predominantly Twisted Square Antiprism Isomers and Circularly Polarized Luminescence

“…This resulted in the chiral cyclen (1,4,7,10-tetraazacyclododecane) compound 3. 3 was reacted with tert-butyl 2-bromoacetate in the presence of potassium carbonate to get the fully protected DOTA compound, and acetate groups were then deprotected under an anhydrous condition 11 which gave L2 after deprotection by TFA. Complexations were performed under neutral conditions.…”

Highly Efficient and Practical Synthesis of the Key Intermediate of Telmisartan

“…Initially, a series of protecting groups on the o-methylaniline 7 were evaluated to secure a selective formylation group at the para position of the amido in 8 for the subsequent reaction. 8 Scheme 2. Improved Process for the Synthesis of the Key Intermediate 1 For the introduction of the formyl group on the benzene ring of 8, the currently common methods include Blanc chloromethylation 9 followed by oxidation, 10 Duff reaction, 11 and Vilsmeier reactions.…”

“…Initially, a series of protecting groups on the o -methylaniline 7 were evaluated to secure a selective formylation group at the para position of the amido in 8 for the subsequent reaction …”

N′-Acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide

“…Hydrolysis methods using sodium acetate are widely used in aromatic acetate deprotection reactions, whereas the ordinarily, stable, aliphatic amides require stronger hydrolysis conditions than the ester motif [10]. In this sense, it could be expected that the mild alkaline and/or no heating conditions could provide the selective hydrolysis of the O-acetyl group from the phenyl acetates of 3-acetyl-5-(3-methyl-1,6-diphenyl-1H-pyrazolo [3,4-…”