67058-58-6

Upstream product

• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 62-53-3 aniline 
• 3507-26-4 2-chloro-6-methylbenzo[d]thiazole 
• 1608-42-0 benzenedizolium-2-carboxylate 
• 13078-28-9 5-(p-tolylamino)-1,2,3,4-thiatriazole 
• 583-68-6 2-bromo-p-toluidine 
• 103-72-0 phenyl isothiocyanate 
• 29289-13-2 2-iodo-4-methylaniline 
• 1145-66-0 1-(4-methylphenyl)-3-phenylthiourea 
• 1397746-40-5 C₁₄H₁₃IN₂S 
• 23451-96-9 2-amino-5-methylthiophenol 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 28899-97-0 triphenylbismuth(V) diacetate 

Downstream Products

• 78072-99-8 (3,6-dimethyl-3H-benzothiazol-2-ylidene)-phenyl-amine 
• 78072-95-4 methyl-(6-methyl-benzothiazol-2-yl)-phenyl-amine 

Relevant academic research and scientific papers

Switchable and Scalable Heteroarylation of Primary Amines with 2-Chlorobenzothiazoles under Transition-Metal-Free and Solvent-Free Conditions

2-Aminobenzothiazoles comprise a valuable structural motif, which prevails in versatile natural products and biologically active compounds. Herein, a switchable and scalable C-N coupling protocol was developed for the synthesis of these compounds from 2-chlorobenzothiazoles and primary amines. Gratifyingly, this protocol was achieved under transition-metal-free and solvent-free conditions. Moreover, introducing an appropriate amount of NaH completely switched the selectivity from mono- toward di-heteroarylation, and further investigations provided a rationale for this new finding. Furthermore, gram-scale synthesis of representative products 3a and 4a was realized by applying operationally simple and glovebox-free procedures, which revealed the practical usefulness of this work. Finally, evaluation of the quantitative green metrics provided evidence that our protocol was superior over the literature ones in terms of green chemistry and sustainability.

Copper/N,N,N',N'-tetramethylethylenediamine-catalyzed synthesis of N-substituted benzoheterocycles via C-S cross-coupling at ambient temperature in water

Copper/N,N,N',N'-tetramethylethylenediamine (Cu/TMEDA)-catalyzed ambient temperature tandem reactions of isothiocyanates with 2-iodophenols or 2-iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2-iminobenzo-1, 3- oxathioles and 2-aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (1mol%) and can yield the products on a gram scale.

Synthesis of N-substituted-2-aminobenzothiazoles using nano copper oxide as a recyclable catalyst under ligand-free conditions, in reusable PEG-400 medium

A simple and practical method for the synthesis of N-substituted-2- aminobenzothiazoles via a cross-coupling reaction of 2-iodo anilines with isothiocyanates is envisaged using nano copper oxide as a recyclable catalyst and Cs2CO3 as a base in PEG-400, as a bio-degradable, reusable, inexpensive and non-toxic reaction medium, under ligand-free conditions. The present tandem process underlines environmental acceptability to access a wide range of N-substituted-2-aminobenzothiazoles in good to excellent yields.

Ligand- and solvent-free synthesis of 2-aminobenzothiazoles by copper-catalyzed tandem reaction of 2-haloanilines with isothiocyanates

We report an environmentally friendly, efficient and practical method for the synthesis of 2-aminobenzothiazoles by a copper(II)-catalyzed tandem reaction of 2-haloanilines with isothiocyanates under ligand- and solvent-free conditions in air. The developed methodology conforms to the principles of 'green chemistry' and addresses the shortage of such methods for the synthesis of 2-aminobenzothiazoles. The reaction is quite general and generates a variety of 2-aminobenzothiazoles in good to excellent yields. Copyright

DDQ-promoted C-S bond formation: Synthesis of 2-aminobenzothiazole derivatives under transition-metal-, ligand-, and base-free conditions

A transition-metal-free method for the intramolecular S-arylation of o-halobenzothiaoureas via DDQ-mediated leading to the 2-aminobenzothiazole derivatives is reported. The reactions are performed at room temperature under ligand- and base-free conditions with good to excellent yields. Georg Thieme Verlag Stuttgart · New York.

Direct transition metal-free C-S bond formation: Synthesis of 2-aminobenzothiazole derivatives via base-mediated approach

A general, efficient, and more practical protocol for the base-mediated intermolecular or intramolecular S-arylation leading to the 2-aminobenzothiazole derivatives is reported. Remarkably, all reactions were carried out under transition-metal-free conditions with good to excellent yields, rendering the methodology presented herein highly valuable from both environmental and economic points of view.

A practical synthesis of 2-aminobenzothiazoles via the tandem reactions of 2-haloanilines with isothiocyanates catalyzed by immobilization of copper in MCM-41

The heterogeneous tandem reactions of 2-haloanilines with isothiocyanates were achieved in DMSO using Et3N as base at 80 °C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(II) complex [MCM-41-2N-CuSO4], yielding a variety of 2- aminobenzothiazoles in good to excellent yields. This heterogeneous copper catalyst exhibited higher activity than CuSO4 and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity.

1,10-Phenanthroline-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in water

The 1,10-phenanthroline-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water is described, which provides an environmentally benign, efficient and simple route for the preparation of 2-aminobenzothiazoles. The present tandem process shows broad substrate scope in the absence of transition metals and phase-transfer catalysts. Copyright

An economically and environmentally sustainable synthesis of 2-aminobenzothiazoles and 2-aminobenzoxazoles promoted by water

Tandem reactions of isothiocyanates (1) with 2-aminothiophenols (2), or isothiocyanates (1) with 2-aminophenols (4), were carried out rapidly and efficiently in water. A significant rate acceleration of the reaction between 1a and 2a in water compared wit

Synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed cross-coupling with part-per-million catalyst loadings

An efficient protocol has been developed for the preparation of 2-aminobenzothiazoles via a copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates at very low catalyst loadings [typically 50ppm of copper(I) iodide (CuI)]. A variety of 2-iodoanilines could be cross-coupled with isothiocyanates, affording 2-aminobenzothiazoles in moderate to good yields (49-93%) under the given conditions. The turnover number (TON) of this reaction reaches 67,000 and the reaction could be scaled up, at least, to the gram-scale. Copyright