5310-14-5

Usage

InChI:InChI=1/C8H9NS/c1-9-8(10)7-5-3-2-4-6-7/h2-6H,1H3,(H,9,10)

Upstream product

• 88070-48-8 N-methylbenzamide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 74-89-5 methylamine 
• 942-91-6 Carboxymethyl dithiobenzoate 
• 16430-05-0 Didehydro-4-methyl-5-phenyl-1,3,4-thiazolidin-2-on 
• 19703-86-7 Didehydro-4-methyl-5-phenyl-1,3,4-thiadiazolidin-2-thion 
• 1280-28-0 Anhydro-5-hydroxy-3-methyl-2-phenylthiazolium hydroxide 
• 89861-53-0 C₁₂H₁₇NS₂ 
• 89861-46-1 N-methyl-N-palmitoyloxythiobenzamide 
• 75-66-1 2-methylpropan-2-thiol 
• 19172-47-5 Lawessons reagent 
• 2446-50-6 N-hydroxy-N-methylbenzamide 
• 100-52-7 benzaldehyde 
• 123-39-7 N-Methylformamide 

Downstream Products

• 58065-86-4 N-methyl-N-trimethylsilanyl-thiobenzamide 
• 31891-19-7 4-carboxy-3-methyl-2-phenyl-4,5-dihydro-thiazolium; bromide 
• 3472-76-2 (dichloro-phenyl-methyl)-carbonimidic acid dichloride 
• 91929-53-2 N-Methyl-thiobenzamid-S-oxyd (N-Methyl-thiobenzoyl-S-oxyd) 
• 26309-44-4 3-methyl-4-phenyl-[1,2,3]dithiazetium; chloride 
• 4115-21-3 N-methyl-N'-tosylbenzimidamide 
• 112423-02-6 3-Methyl-6-oxo-2,5-diphenyl-6H-1,3-thiazin-3-ium-4-olat 
• 133386-66-0 N-(Cyclohex-1-enoyl)-N-methylthiobenzamide 
• 88295-93-6 N-Methacryloyl-N-methylthiobenzamide 
• 63182-88-7 N,S-Dimethylthiobenzamidiumiodid 
• 59073-76-6 N-Methyl-thiobenzimidic acid methyl ester; hydriodide 
• 89861-52-9 N-Methyl-thiobenzimidic acid tert-butyl ester 
• 121089-80-3 N-Methyl-N-thiobenzoyl-acetamide 
• 121019-22-5 4-acetylthio-1,3,3-trimethyl-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur

A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.

Method for preparing aryl thioamide compound

The invention discloses a method for preparing an aryl thioamide compound. The method comprises the following steps: under the protection of inert gas, performing stirring to react for 6-12 hours at the reaction temperature of room temperature to 60 DEG C by taking aryl methanol as a substrate, sublimed sulfur as a sulfur source, an alkali metal complex formed by combining alkali metal salt and ligand as a catalyst, alkali as an accelerant, formamide as a solvent and an amine source; and carrying out post-treatment on the reaction product to obtain the aryl thioamide compound. According to theinvention, cheap and easily available aryl methanol is used as a substrate for three-component reaction to prepare the corresponding thioamide compound; the method for preparing the aryl thioamide compound has the technical advantages of simple technological process, high yield, less pollution, safety, environmental protection, greenness, mildness and the like.

Oxidative Coupling-Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides

An efficient and selective multicomponent oxidative coupling, involving the use of two different amines, sodium phosphate, and elemental sulfur have been described for the preparation of thioamides, employing microwave irradiation. The use of an iron(III)-based imidazolium salt is essential as catalyst. Indeed, the iron-based catalyst is involved in the oxidative coupling of the two amines and in the subsequent C-S bond formation. The protocol is useful for a wide variety of primary benzylamines and alkylamines, as coupling partners. Thus, various electron-rich and electron-poor substituents in the aromatic rings and also fused piperidine derivatives, are suitable starting materials in this reaction. Some of the obtained products are important synthetic intermediates for natural products.

Transition-Metal-Free Cleavage of C-C Triple Bonds in Aromatic Alkynes with S8 and Amides Leading to Aryl Thioamides

A novel transition-metal-free cleavage reaction of C-C triple bonds in aromatic alkynes with S8 and amides furnishes aryl thioamides in moderate to excellent yields. The remarkable features of this thioamidation include the metal-free cleavage of C-C triple bond, mild reaction conditions, as well as wide substrate scope that is particularly compatible with some internal aromatic alkynes and acetamides.

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO2 extrusion followed by insertion of isothiocyanates

A new palladium mediated “one pot” synthesis of thioamides from aromatic carboxylic acids (ArCO2H + RNCS → ArC(S)NHR + CO2) was discovered by gas-phase experiments and theoretical studies. Palladium-mediated decarboxylation of aromatic carboxylic acids followed by addition of substituted isothiocyanates leads to the corresponding thioamide derivatives.

A multipathway coupled domino strategy: I2-mediated oxidative thionation for direct synthesis of thiobenzamides from miscellaneous substrates

An efficient iodine-mediated multipathway coupled domino reaction has been developed for the synthesis of thiobenzamides from benzylamines, benzylamines/aldehydes, and N-alkyl benzylamines under the same reaction conditions. This approach combines two consecutive domino processes in one pot using iodine as the oxidant.

Desulfurization and H-migration of secondary thioamides catalyzed by an iron complex to yield imines and their reaction mechanism

Secondary thioamides were converted into imines as the major products using hydrosilane in the presence of an iron catalyst. An iron carbene complex with a silyl thiolato ligand was isolated as one of the intermediates of the catalytic cycle and was characterized by X-ray analysis.

Microwave-assisted synthesis of thioamides with elemental sulfur

Thioamides are prepared in moderate-to-good yields from the benzylamines or benzylamine derivatives by treatment with elemental sulfur under microwave and solvent-free conditions at 170.C in 15 min.