5310-26-9

Usage

InChI:InChI=1/C14H13NOS/c1-16-13-9-7-12(8-10-13)15-14(17)11-5-3-2-4-6-11/h2-10H,1H3,(H,15,17)

Upstream product

• 7472-54-0 N-(p-methoxyphenyl)benzamide 
• 936-61-8 Thiobenzoic acid O-ethyl ester 
• 101960-60-5 [(Z)-4-Methoxy-phenylimino]-phenyl-acetic acid 
• 949-00-8 phenyl dithiobenzoate 
• 104-94-9 4-methoxy-aniline 
• 20876-81-7 p-tolyl benzodithioate 
• 77069-61-5 Dithiobenzoic acid 4-chloro-phenyl ester 
• 165543-83-9 4-bromophenyl dithiobenzoate 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 65-85-0 benzoic acid 
• 21258-08-2 N-(4-anisyl)-N'-benzoylthiourea 
• 103-82-2 phenylacetic acid 
• 5470-34-8 4-methoxyformanilide 

Downstream Products

• 10205-69-3 6-methoxy-2-phenylbenzothiazole 
• 7472-54-0 N-(p-methoxyphenyl)benzamide 
• 12091-75-7 4-amino-3-(4-methoxy-phenyl)-2-phenyl-thiazolium; chloride 
• 14156-57-1 S-phenyl-N-p-methoxyphenylisothiobenzamide 
• 12113-20-1 4-acetylamino-3-(4-methoxy-phenyl)-2-phenyl-thiazolium; chloride 
• 7459-69-0 benzyl thionobenzoate 
• 262365-82-2 (Z)-3-[4-methoxyphenylamino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-one 
• 1609960-03-3 N-(4-methoxyphenyl)-N-p-tolylsulfanylmethyl thiobenzamide 
• 1122660-11-0 3-[3-(4-methoxyphenyl)-[1,2,4]-thiadiazol-5-yl]phenol 
• 33670-44-9 6-hydroxy-2-phenylbenzothiazole 
• 79229-99-5 (Z)-N-(4'-methoxyphenyl)methyl-3-amino-3-phenyl acrylate 
• 31789-69-2 N²-p-Toluolsulfonyl-N¹-(p-methoxyphenyl)benzamidin 

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.

Economic Sulfur Conversion to Functional Polythioamides through Catalyst-Free Multicomponent Polymerizations of Sulfur, Acids, and Amines

Sulfur utilization is a global concern because of its abundant nature sources and the safety or environmental problems caused by its burning or oxidation during storage, while sulfur-containing polymers are popular materials in virtue of their fascinating

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.).

Catalyst- and Supporting-Electrolyte-Free Electrosynthesis of Benzothiazoles and Thiazolopyridines in Continuous Flow

A catalyst- and supporting electrolyte-free method for electrochemical dehydrogenative C?S bond formation in continuous flow has been developed. A broad range of N-arylthioamides have been converted to the corresponding benzothiazoles in good to excellent yields and with high current efficiencies. This transformation is achieved using only electricity and laboratory grade solvent, avoiding degassing or the use of inert atmosphere. This work highlights three advantages of electrochemistry in flow, which is (i) a supporting electrolyte-free reaction, (ii) an easy scale-up of the reaction without the need for a larger reactor and, (iii) the important and effective impact of having a good mixing of the reaction mixture, which can be achieved effectively with the use of flow systems. This clearly improves the reported methods for the synthesis of benzothiazoles.

Sulfur promoted decarboxylative thioamidation of carboxylic acids using formamides as amine proxy

An efficient decarboxylative thioamidation of arylacetic and cinnamic acids has been developed employing formamides as amine surrogate and sulfur as promoter. Thioamides with variant structural features are obtained under mild reaction conditions without the use of transition metal catalysts and oxidants.

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.

On the synthesis of α-amino sulfoxides

A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successfully prepared and isolated. It is speculated that four other α-amino sulfoxides were synthesised but could not be isolated due to their propensity to α-eliminate the sulfoxide. Ultimately, a stable, cyclic N-Boc α-amino sulfoxide was prepared and this successful synthesis relied on the α-amino sulfoxide being part of a bicyclic [3.1.0] fused ring system that could not undergo α-elimination of the sulfoxide. the Partner Organisations 2014.

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.