5310-28-1

Usage

InChI:InChI=1/C13H10ClNS/c14-11-6-8-12(9-7-11)15-13(16)10-4-2-1-3-5-10/h1-9H,(H,15,16)

Upstream product

• 936-61-8 Thiobenzoic acid O-ethyl ester 
• 2866-82-2 N-(4-chlorophenyl)benzamide 
• 59819-37-3 4-N,N-dimethylamino-2-N-phenylamino-1-thia-3-azabutadiene 
• 34918-76-8 N-(4-Chloro-phenyl)-benzimidoyl chloride 
• 949-00-8 phenyl dithiobenzoate 
• 106-47-8 4-chloro-aniline 
• 20876-81-7 p-tolyl benzodithioate 
• 77069-61-5 Dithiobenzoic acid 4-chloro-phenyl ester 
• 165543-83-9 4-bromophenyl dithiobenzoate 
• 75-15-0 carbon disulfide 
• 7035-69-0 N-(4-chlorophenyl)benzamidine 
• 100-52-7 benzaldehyde 
• 4921-83-9 1-benzoyl-3-(4-chloro-phenyl)-thiourea 
• 98-88-4 benzoyl chloride 

Downstream Products

• 7466-32-2 6-chloro-2-phenylbenzo[d]thiazole 
• 12087-84-2 4-amino-3-(4-chloro-phenyl)-2-phenyl-thiazolium; chloride 
• 26245-44-3 3-(4-chloro-phenyl)-4-oxo-2-phenyl-4,5-dihydro-thiazolium betaine 
• 2866-82-2 N-(4-chlorophenyl)benzamide 
• 52718-80-6 5-acetyl-3-(4-chloro-phenyl)-4-oxo-2-phenyl-4,5-dihydro-thiazolium betaine 
• 63566-55-2 2-(4-chlorophenyl)-1H-isoindole-1,3(2H)-dithione 
• 12117-29-2 4-acetylamino-3-(4-chloro-phenyl)-2-phenyl-thiazolium; chloride 

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.

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.

Transition metal-free α-Csp3-H oxidative sulfuration of benzyl thiosulfates with anilines to form N-aryl thioamides

A metal-free approach to N-aryl thioamides from Bunte salts and anilines in DMSO has been developed. This method tolerated a wide range of functional groups on the aromatic ring, providing an ideal way to N-aryl thioamides in good to excellent yields from cheap and easily available starting materials. A plausible mechanism was also proposed based on the X-ray single crystal diffraction, NMR and MS analyses of DMSO-concerning intermediates.

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.).

Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds

Upon treatment with trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate (TFDA) and a catalytic amount of N,N,N′,N′-tetramethyl-1,8-diaminonaphthalene, secondary thioamides and thiocarbamates undergo selective difluoromethylation on the sulfur atom to give S-difluoromethyl thioimidates and thioiminocarbonates in good yields, respectively. This is the first report on the synthesis of acyclic difluoromethyl thioimidates and thioiminocarbonates. The key for S-difluoromethylation is the organocatalytic generation of difluorocarbene (:CF2) under mild conditions, which prevents decomposition of the substrates. This process provides an efficient approach to pharmaceuticals and agrochemicals bearing a difluoromethylsulfanyl group, starting from widely available thiocarbonyl compounds.

Decomposition of benzoylthioureas into benzamides and thiobenzamides under solvent-free conditions using iodine-alumina as the catalyst and its mechanistic study by density functional theory

The breaking down of benzoylthioureas to benzamides and thiobenzamides in a single route using iodine-alumina as the catalyst under solvent-free conditions is highlighted. Results show that when an electron donating group, such as the methyl or methoxy group, is at the para-position of the aryl group of 1, benzamide (2) is the favoured product. When an electron withdrawing group, such as the chlorine or nitro group, is at the para-position of the aryl group of 1, thiobenzamide (3) is the favoured product. From the study of the reaction mechanism, it may be postulated that the formation of benzamide is due to the migration of the aryl group, whereas the formation of thiobenzamide may be due to the migration of the phenyl group. Thus, a new method for the formation of benzamides and thiobenzamides was developed.

Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation

An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.

Nano n -propylsulfonated magnetic γ-Fe2O3 as an efficient and reusable catalyst for the synthesis of thioamides

One-pot three-component reactions of aldehydes, amines, and sulfur are carried out in the presence of nano n-propylsulfonated magnetic γ-Fe2O3 as a catalyst for the synthesis of biologically interesting thioamide derivatives. The value of this catalytic method lies in its mild reaction catalyst and conditions, good yields, and ease of handling.

Sulfonic acid functionalized nano Γ-Al 2O 3: A new, efficient, and reusable catalyst for synthesis of thioamides

Sulfonic acid functionalized nano γ-Al2O3 is easily prepared by the reaction of nano γ-Al2O3 with 1,3-propane sulfone. This reagent can be used as an eficient catalyst for the synthesis of thioamides. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered for several times.