2314-17-2

Usage

InChI:InChI=1/C11H13NS2/c1-2-3-8-13-11-12-9-6-4-5-7-10(9)14-11/h4-7H,2-3,8H2,1H3

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 109-69-3 n-Butyl chloride 
• 149-30-4 2-Mercaptobenzothiazole 
• 109-65-9 1-bromo-butane 
• 137-07-5 2-amino-benzenethiol 
• 95-16-9 1,3-Benzothiazole 
• 26726-20-5 sodium n-butylsulfanesulfonate 
• 1123-99-5 2-iodobenzothiazole 
• 20637-27-8 2-deuteriobenzothiazole 
• 109-79-5 n-butanethiol 
• 629-45-8 dibutyl disulfide 
• 542-69-8 1-iodo-butane 
• 102-85-2 tri-n-butyl phosphite 
• 102-77-2 4-(benzothiazole-2-sulfenyl)-morpholine 

Downstream Products

• 21261-91-6 3-Butyl-benzothiazolin-2-thion 
• 40115-03-5 2-cyclohexyl-benzothiazole 

Relevant academic research and scientific papers

Ag-Cu copromoted direct C2-H bond thiolation of azoles with Bunte salts as sulfur sources

A direct C2-H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts. This protocol could furnish various substituted 2-thioazoles in moderate to good yields. This method has a broad substrate scope and shows good functional group tolerance.

Selective and mild sulfoxidation of 2-sulfylbenzothiazole using hydroperoxides derived from cyclohexanone in the absence of catalyst

Alkyl hydroperoxides derived from cyclohexanone are attractive oxidants because they are easily available, more reactive than TBHP but much less acidic than m-CPBA. Wherein 1,1′-peroxybis(1-hydroperoxycyclohexane) (C) can be generated by the current simply method and displays the excellent reactivity and selectivity based on oxidative reactions of various benzothiazolyl sulfides substituted by different function groups. The research found that the reactions can be performed in the absence of catalyst and under very mild conditions optimized. Yields of sulfoxides is higher than 90%, no or a little reaction happened at the proximal double bond、 N and S atoms in the benzothiazolyl moiety. Phenyl sulfide as the substrates was also examined for the reaction scope test. The results show that they were uniquely and completely oxidized to sulfoxides in 1 h. A mild, environmentally friendly, catalyst-free aryl sulfide sulfoxidation method has been developed.

Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media

A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.

Preparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow

We report the preparation of lithium-salt-free KDA (potassium diisopropylamide; 0.6 m in hexane) complexed with TMEDA (N,N,N′,N′-tetramethylethylenediamine) and its use for the flow-metalation of (hetero)arenes between ?78 °C and 25 °C with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min?1 using a commercial flow setup. The resulting potassium organometallics react instantaneously with various electrophiles, such as ketones, aldehydes, alkyl and allylic halides, disulfides, Weinreb amides, and Me3SiCl, affording functionalized (hetero)arenes in high yields. This flow procedure is successfully extended to the lateral metalation of methyl-substituted arenes and heteroaromatics, resulting in the formation of various benzylic potassium organometallics. A metalation scale-up was possible without further optimization.

One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water

A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.

Novel 3-methyl-2-alkylthio benzothiazolyl-based ionic liquids: Synthesis, characterization, and antibiotic activity

Three series of novel 3-methyl-2-alkylthio benzothiazolyl ionic liquids (ILs) were synthesized for the first time. After structural identification, their melting point, solubility, and thermostability together with antibiotic activity were determined successively. As a result, 3-methyl-2-alkylthio benzothiazolyl p-toluene sulfonate was found to have the highest antibacterial activity among the three series of ILs. Meanwhile, it has a good solubility in water as well. On the basis of comprehensive comparison with similar compounds, the effect of cations and anions of these benzothiazolium ILs on typical physical properties together with antibiotic performance was explored and discussed, which is very beneficial to take the greatest advantage of their structural designability for various purposes. Furthermore, the experiment data preliminarily discovered the relationships of the structure-properties/activities of the above three kinds ILs to a certain extent, which can provide useful references for future research and for the potential application of these new ILs as surfactant antiseptics or agricultural chemicals.

A method for synthesis of aryl thioether compound

The invention discloses a synthetic method of an aryl thioether compound as shown in a formula (3). The polysubstituted aryl thioether compound is obtained by using aryl iodide or an aryl trifluoromethane sulphonate derivative and halogenated hydrocarbon as reaction raw materials and Na2S2O3 as a vulcanization reagent and reacting in a reaction solvent under the effect of a metal palladium catalyst. The synthetic method is mild in reaction conditions, simple in reaction operation and relatively high in productivity, can provide key skeleton structures for synthesis of lots of natural products and medicines and can be widely applied to industrialization scale production.

Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na2S 2O3 as a sulfurating reagent

The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na 2S2O3·5H2O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O 3·5H2O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.

Copper oxide nanoparticle-catalyzed chalcogenation of the carbon-hydrogen bond in thiazoles: Synthesis of 2-(organochalcogen) thiazoles

We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/dio-rganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydro-gen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromat-ic ring bonded to the chalcogen atom of diorganyl di-chalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.

Lewis acid-catalyzed, copper(II)-mediated synthesis of heteroaryl thioethers under base-free conditions

A Lewis acid (AgI, NiII, or FeII) catalyzed, CuII-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic methyl thioethers.