16954-69-1

Usage

Uses

Used in Pharmaceutical Industry:
N-methylbenzothiazol-2-amine is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, N-methylbenzothiazol-2-amine is employed as a building block in the creation of agrochemicals, aiding in the development of pesticides and other agricultural chemicals to protect crops and enhance yield.
Used in Dye Industry:
N-methylbenzothiazol-2-amine is utilized as a key component in the production of dyes, providing color and stability to various products in the textile, printing, and other industries.
Used in Rubber Industry:
As a rubber accelerator, N-methylbenzothiazol-2-amine is used to speed up the vulcanization process, improving the efficiency and performance of rubber products. Additionally, it serves as a component in the production of antioxidants and antidegradants, enhancing the durability and longevity of rubber goods.

InChI:InChI=1/C8H8N2S/c1-9-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H,9,10)

Upstream product

• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 74-89-5 methylamine 
• 4104-75-0 1-methyl-1-phenylthiourea 
• 2724-69-8 1-methyl-3-phenylthiourea 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 57-14-7 N,N-Dimethylhydrazine 
• 615-43-0 2-iodophenylamine 
• 598-52-7 1-(methyl)-thiourea 
• 34551-29-6 4-methyl-5-phenylimino-Δ²-1,2,3,4-thiatriazoline 
• 1843-21-6 N-phenyl-2-benzothiazolamine 
• 141-52-6 sodium ethanolate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 136-95-8 2-aminobenzothiazole 

Downstream Products

• 18691-97-9 methabenzthiazuron 
• 58663-62-0 benzothiazol-2-yl-methyl-carbamic acid methyl ester 
• 132509-67-2 N-methyl-6-nitrobenzo[d]thiazol-2-amine 
• 19777-08-3 N-(benzo[d]thiazol-2-yl)-N-methylbenzamide 
• 53004-69-6 benzothiazol-2-yl-methyl-nitroso-amine 
• 107470-36-0 1-{2-[(Z)-Methylimino]-benzothiazol-3-yl}-3-phenoxy-propan-2-ol 
• 22258-71-5 3-(β-chloroethyl)benzothiazolin-2-one 
• 118215-11-5 N-Benzothiazol-2-yl-N-methyl-thiobenzamide 
• 92969-18-1 1-benzothiazol-2-yl-2-benzyl-1-methyl-isothiourea 
• 90349-90-9 N--N-methyl-thiocarbamid 
• 53065-94-4 1-benzothiazol-2-yl-1-methyl-urea 
• 53159-45-8 1-Benzthiazol-1yl-1-methyl-3-hydroxymethylharnstoff 
• 53065-93-3 N-(benzothiazolyl-2)-N-methylformamid 
• 134794-08-4 N-(benzothiazol-2-yl)-N-methyl-N'-phenylsulfonylurea 

Relevant academic research and scientific papers

One-pot synthesis of 2-aminobenzothiazoles using a new reagent of [Bmim]Br3 in [Bmim]BF4

The one-pot direct synthesis of 2-aminobenzothiazoles from phenyl isothiocyanate and amines using a new reagent of 1-butyl-3-methylimidazolium tribromide ([Bmim]Br3) in ionic liquid 1-butyl-3-methyl-imidazolium tetraflouoroborate ([Bmim]BF4) is described.

Synthesis and properties of esters of benzothiazolylamino(imino)propionic acids

Reaction of 2-alkylaminothiazoles with methyl acrylate leads predominantly to the formation of N-alkyl-N-(β-methoxycarbonylethyl)-2-aminobenzothiazoles on boiling or to 2-(alkylimino)-3-(β-methoxycarbonylethyl)-benzothiazolines at room temperature. A complex mixture of products was obtained from unsubstituted 2-aminobenzothiazole and methyl acrylate, of which the main was 2-oxo-3,4-dihydro-2H-pyrimido[2,1-b]benzothiazole. Complete or partial destruction of the benzothiazolines occurred on heating to 140°C. 1998 Plenum Publishing Corporation.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate

An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete selectivities and functional group friendliness. Furthermore, the synthesized catalyst could be recycled by simple filtration without obvious loss of catalytic activity after sixth cycle. Notably, this research exhibited the potential of covalent triazine framework-supported transition metal catalysts for hydrogen autotransfer process.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.

C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates

Benzothiazoles undergo regioselective C2-H functionalization with triphenylphosphine to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- A nd N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in the reduction of the benzothiazole, which is useful for specific C2 deuteration of benzothiazoles.

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin

A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).

Convenient and reliable routes towards 2-aminothiazoles: Palladium-catalyzed versus copper-catalyzed aminations of halothiazoles

Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key molecules in pharmaceutical research. Copyright