5397-16-0

Upstream product

• 50-84-0 2,4 dichlorobenzoic acid 
• 100-46-9 benzylamine 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 180069-53-8 (E)-N-benzyl-1-(2,4-dichlorophenyl)methanimine 
• 89-75-8 2,4-dichlorobenzoyl chloride 

Downstream Products

• 106841-13-8 N-benzyl-4-chloro-2-hydroxybenzamide 
• 213475-01-5 {4-[(2,4-Dichloro-benzoylamino)-methyl]-benzenesulfonylamino}-acetic acid 
• 126571-89-9 N-(4-chlorosulfonylphenylmethyl)-2,4-dichlorobenzamide 

Relevant academic research and scientific papers

Visible-Light-Mediated Synthesis of Amides from Aldehydes and Amines via in Situ Acid Chloride Formation

An efficient visible-light photocatalysis-based one-pot amide synthesis method was developed; visible-light irradiation of a mixture of an aldehyde, tert-butyl hydrogen peroxide, and N-chlorosuccinimide using a Ru(bpy)3Cl2 photocatalyst afforded an acid chloride, which subsequently reacted with amine to yield the corresponding amide. The reaction was used to synthesize moclobemide and a D3 receptor intermediate.

A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water

An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.

Oxidation of N-benzylaldimines to N-benzylamides by MCPBA and BF3·OEt2

N-Benzylamides were obtained from the corresponding N-benzylaldimines in high yields. N-Benzylaldimines are readily prepared from the corresponding aldehydes with benzylamine. This procedure involves the oxidation of N-benzylaldimines with MCPBA with BF3·OEt2. In this reaction, the reaction presumably follows an internal hydrogen abstraction to provide only N-benzylamide.

A useful acylation method using trichloroacetonitrile and triphenylphosphine for solid phase organic synthesis

A novel acylation procedure was developed for polymer supported synthesis, with in situ generated acyl chlorides using trichloroacetonitrile and triphenylphosphine.

CHLOROSULFONATION OF N-BENZYL CARBOXAMIDES

N-benzyl p-chloro- and 2,4-dichloro-benzamide (3,4) reacted with chlorosulfonic acid to give the corresponding p-sulfonyl chlorides (6,7).On the other hand, N-benzylthiophen-2-carboxamide (5) afforded the 2.41-disufonyl chloride (21).The sulfonyl chlorides (6,7,21) were condensed with nucleophiles to give 22 derivatives.The spectral data of the compounds are briefly discussed, together with the results of preliminary bioligical screening against fungi, insects and weeds.Keywords: Chlorosulfonation of: N-benzyl-p-chlorobenzamide (3); N-benzyl-2,4-dichlorobenzamide (4); N-benzylthiophen-2-carboxamide (5).