95468-72-7

Upstream product

• 52807-29-1 N-(4-iodophenyl)benzamide 
• 540-37-4 p-aminoiodobenzene 
• 98-88-4 benzoyl chloride 
• 150-60-7 dibenzyl disulphide 

Downstream Products

• 883-93-2 2-Phenylbenzothiazole 
• 1082536-19-3 6-iodo-2-phenylbenzo[d]thiazole 
• 52807-29-1 N-(4-iodophenyl)benzamide 

Relevant academic research and scientific papers

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson's reagent

After completing the thio-substitution with Lawesson's reagent, ethanol was found to be effective in the decomposition of the inherent stoichiometric six-membered-ring byproduct from the Lawesson's reagent to a highly polarized diethyl thiophosphonate. The treatment significantly simplified the following chromatography purification of the desired thioamide in a small scale preparation. As scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including a traditional phase separation, extraction, and recrystallization. The newly developed chromatography-free procedure did not generate P-containing aqueous waste, and only organic effluents were discharged. It is believed that the optimized procedure offers the great opportunity of applying the Lawesson's reagent for various thio-substitution reactions on a large scale.

Sulfur-Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles

In the presence of catalytic amounts of elemental sulfur, dibenzyl disulfide/DMSO was found to be an excellent thiobenzoylating agent of amines to provide a wide range of thioamides. The reaction becomes autocatalytic when anilines substituted by an o-cyclizable group were used as nucleophile, leading to the corresponding 2-aryl aza heterocycles. (Figure presented.).

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Palladium-catalyzed C-H cyclization in water: A milder route to 2-arylbenzothiazoles

Water was successfully employed as a reaction medium in palladium-catalyzed C-H cyclization of thiobenzanilides. Reactions efficiently proceeded under considerably mild conditions such as 40 °C in water, providing a more practical, greener method for the synthesis of 2-arylbenzothiazoles. For some substrates, the addition of an amphiphilic surfactant greatly enhanced the process. The method represents a rare example of palladium-catalyzed C-H functionalization processes performed in water. Georg Thieme Verlag Stuttgart · New York.

Palladium-catalyzed synthesis of 2-substituted benzothiazoles via a C-H functionalization/intramolecular C-S bond formation process

(Chemical Equation Presented) Catalytic synthesis of 2-substituted benzothiazoles from thiobenzanilides was achieved in the presence of a palladium catalyst through C-H functionalization/C-S bond formation. This method features the use of a novel catalytic system consisting of 10 mol % of Pd(II), 50 mol % of Cu(I), and 2 equiv of Bu4NBr that produced variously substituted benzothiazoles in high yields with good functional group tolerance.