2941-71-1

Usage

Chemical Properties

Pale yellow solid

InChI:InChI=1/C9H9NS/c1-6-3-4-8-9(5-6)11-7(2)10-8/h3-5H,1-2H3

Upstream product

• 5310-17-8 N-(p-tolyl)ethanethioamide 
• 108-24-7 acetic anhydride 
• 23451-96-9 2-amino-5-methylthiophenol 
• 103-89-9 4-Methylacetanilide 
• 62-55-5 thioacetamide 
• 141-82-2 malonic acid 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 3288-13-9 diethyl (4-methylphenyl)thiocarbamamoylmalonate 
• 837392-69-5 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole 
• 74-88-4 methyl iodide 
• 614-83-5 2-bromo-4-methylacetanilide 
• 2466-76-4 N-Acetylimidazole 
• 29289-16-5 N-(2-iodo-4-methylphenyl)acetamide 
• 22100-68-1 2,2'-dicyano-3,3'-bis-(4-methyl-anilino)-3,3'-disulfanediyl-bis-acrylic acid diethyl ester 

Downstream Products

• 686747-48-8 7-nitro-2,6-dimethylbenzothiazol 
• 102452-92-6 2-[bis-(4-nitro-phenylazo)-methylene]-3,6-dimethyl-2,3-dihydro-benzothiazole 

Relevant academic research and scientific papers

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles

An efficacious and mild KOtBu-promoted intramolecular C-S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.

Efficient CDI/CH3SO3H-catalyzed, microwave-assisted synthesis of 2-substituted benzothiazoles

CDI combined with CH3SO3H was found to be highly effective for the cyclization of 2-aminothiophenol derivatives with carboxylic acids under MW condition. Fourteen benzothiazole derivatives were synthesized in good yield and their structures were characterized by1H-NMR,13C-NMR, IR and mass spectrometry. This simple, rapid synthetic method is believed to provide a useful process for the synthesis of 2-substituted benzothiazole compounds.

Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters

A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.

Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization

A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.

Solid phase synthesis of benzothiazole and thiophene derivatives based on resin-bound cyclic malonic acid ester

A new method for the solid phase synthesis of benzothiazoles and 2-arylamino-3-carboxyl-4-hydroxy-5-arylthiophenes is described. Resin bound cyclic malonic acid ester was reacted with aryl isothiocyanates and then with bromine or α-bromoketones, followed by treatment with perchloric acid or sodium methoxide to afford substituted 2-methylbenzothiazoles or 2-arylamino-3-carboxyl-4-hydroxy-5-arylthiophenes, respectively, in high yields and purities.

Condensation of thioamides with 2-aminothiophenols: A versatile synthesis of benzothiazoles

Thioamides condense with 2-aminothiophenols under convenient and mild conditions to provide a variety of simple and functionalized benzothiazoles in fair to good yields.

Photochemical Synthesis of Benzothiazoles

Irradiation of o-halothioacetanilides (1a-p) affords benzothiazoles (2a-p) in general.In methanol medium, polyhalogenated thioacetanilides yield benzothiazoles with the loss of bromine atom in the 4- or 6-position of the benzothiazole.Arylation of benzothiazoles occurs in benzene medium.