6244-75-3

Upstream product

• 6833-15-4 4-chlorobenzanilide 
• 133218-29-8 p-Chloro-N-(3-phenylpropionyl)thiobenzanilide 
• 39153-42-9 p-Chlor-dithiobenzoesaeure-p-chlorphenylester 
• 62-53-3 aniline 
• 20849-33-6 phenyl p-chlorobenzenedithiocarboxylate 
• 165543-77-1 4-Chloro-dithiobenzoic acid p-tolyl ester 
• 165543-78-2 4-Chloro-dithiobenzoic acid 4-bromo-phenyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 55712-14-6 2-(4-chloro-phenyl)-4,6-dioxo-3,5-diphenyl-5,6-dihydro-4H-[1,3]thiazinium betaine 
• 61522-25-6 2-(4-chloro-phenyl)-5-ethoxycarbonyl-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine 
• 52730-98-0 2-(4-Chlorphenyl)-3,5-diphenyl-1,3-thiazolium-4-olat 
• 52730-97-9 2-(4-chloro-phenyl)-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine 
• 136169-38-5 C₁₃H₁₂ClN₃ 
• 133218-29-8 p-Chloro-N-(3-phenylpropionyl)thiobenzanilide 
• 6265-91-4 2-(4-chlorophenyl)benzothiazole 
• 136169-34-1 C₂₀H₁₇ClN₄O 
• 136169-25-0 C₂₀H₁₇ClN₄S 
• 6833-15-4 4-chlorobenzanilide 

Relevant academic research and scientific papers

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

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.

Synthesis of thioamides by catalyst-free three-component reactions in water

Three-component reactions involving amines, aldehydes, and elemental sulfur powder are reported to afford thioamides in a simple one-pot procedure in the absence of a catalyst. A variety of thioamides can be obtained in good to excellent yields up to 88 %. Three-component reactions involving amines, aldehydes, and sulfur powder afford thioamides in a simple one-pot procedure. A variety of substituted thioamides are obtained in good to excellent yields up to 88 %. Copyright

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.

Kinetics and mechanism of the aminolysis of phenyl dithiobenzoates

The kinetics and mechanism of the reactions of phenyl dithiobenzoates with anilines in acetonitrile at 55.0 deg C have been studied.The large magnitude of βx(βnuc) and the signs of cross-interaction constants, ρeXY > 0, ρYZ XZ > 0, are all consistent with the carbonyl addition mechanism in which the breakdown of the tetrahedral intermediate, T+/-, is rate limiting.The thiocarbonyl group (C=S) is found to favour amine expulsion in contrast to the carbonyl group (C=O) which favours the S-bonded nucleofuge expulsion from T+/-.The signs of cross-interaction constants, ρXY, ρYZ and/or ρXZ, are shown to provide useful mechanistic criteria for distinguishing, especially, the carbonyl addition mechanism involving the rate-limiting breakdown of the tetrahedral intermediate (T+/- from the concerted SN2 mechanism.

Photochemical δ-Hydrogen Abstraction from Acyclic and Semicyclic Monothioimides

Photochemical δ-hydrogen abstraction from acyclic and semicyclic monothioimides have been studied.Photolysis of acyclic monothioimides possessing a benzylic hydrogen atom at the δ-position gave γ-lactams, via a 1,5-diradical intermediate, accompanied by thioamides were generated by γ-hydrogen abstraction.Irradiation of the five-membered semicyclic monothioimide, N-(3-phenylpropionyl)pyrrolidine-2-thione, yielded 5-mercapto-4-phenyl-1-azabicyclooctan-2-one.For N-(3-phenylbutyryl)pyrrolidine-2-thione, disproportionation, involving 1,6-hydrogen migration, was the main path.Photolysis of the six-membered semicyclic monothioimide, N-(3-phenylbutyryl)piperidine-2-thione, gave an unsaturated thiol, via a 1,4-hydrogen shift of a 1,5-diradical intermediate, accompanied by cyclisation product and piperidine-2-thione.

ANTIMYCOBACTERIAL THIOBENZANILIDES

A group of 30 thiobenzanilides active against Mycobacterium kansasii have been synthesized and their 1H NMR and UV spectra and RM values (TLC on silica gel impregnated with methylsilicone oil) have been measured.From the correlation between the chemical shifts of the thioamide proton in the 1H NMR spectra and the Hammett constants it can be concluded that the substituents in both aromatic rings uniformly affect the electron density of the thioamide group.The antimycobacterial activity is probably connected with local molecular parameters and can be considered to be approximately additive with respect to both parts of the molecule.