61249-37-4

Usage

InChI:InChI=1/C14H11ClN2S/c15-11-6-7-12-13(8-11)18-14(17-12)16-9-10-4-2-1-3-5-10/h1-8H,9H2,(H,16,17)

Upstream product

• 39536-21-5 S-methyl N-(4-chlorophenyl)amidino thioether 
• 74063-19-7 7-chloro-3(methylthio)-1,2,4-benzothiadiazine 1-oxide 
• 622-79-7 benzyl azide 
• 95-24-9 6-chloro-2-aminobenzothiazole 
• 100-51-6 benzyl alcohol 
• 88333-03-3 Benzyl isocyanide 
• 3292-54-4 6-chloro-3H-benzo[d][1,2,3]dithiazole 2-oxide 
• 35576-53-5 6-Chloro-1,2,3-benzodithiazol-1-ium chloride 
• 106-47-8 4-chloro-aniline 
• 1642135-39-4 C₁₄H₁₀ClIN₂ 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 100-46-9 benzylamine 
• 74063-12-0 N-<7-chloro-3-(methylthio)-1,2,4-benzothiadiazin-1-ylidene>-p-toluenesulfonamide 
• 74063-20-0 7-chloro-3-(benzylamino)-1,2,4-benzothiadiazine 1-oxide 

Relevant academic research and scientific papers

Metal-Free Synthesis of 2-Aminobenzothiazoles via Iodine-Catalyzed and Oxygen-Promoted Cascade Reactions of Isothiocyanatobenzenes with Amines

In this paper, a highly efficient and sustainable synthesis of 2-aminobenzothiazoles through the cascade reactions of isothiocyanatobenzenes with primary or secondary amines by using iodine as a catalyst and oxygen as an oxidant is presented. Mechanistically, the formation of the title compounds involves the in situ formation of the required benzothiourea intermediate followed by its intramolecular cross dehydrogenative coupling of a C(sp2)-H bond and a S-H bond. To our knowledge, this should be the first example in which 2-aminobenzothiazoles are efficiently prepared from simple and cheap isothiocyanates and amines under metal-free conditions by using iodine as a catalyst and molecular oxygen as an oxidant with water as the byproduct. Compared with literature protocols, this method eliminates the use of ortho-halo-substituted precursors, expensive transition-metal catalysts, and hazardous oxidants.

Synthesis method of 2-aminobenzothiazole compounds

The invention discloses a preparation method of 2-aminobenzothiazole compounds. The 2-aminobenzothiazole compounds is prepared from the following steps of dissolving phenyl/naphthalene isothiocyanateand primary amine into a solvent, adding a catalyst iodine and an oxidant, carrying out one-pot multi-step tandem reaction to prepare the 2-aminobenzothiazole compounds under the temperature of 80 to 150 DEG C. The synthesis method has the advantages that raw materials are cheap and easily available, the reaction condition is mild, the substrate application range is broad, atom economy is high, requirements of green chemical are met, and a novel method which is economical and practical and green and environmentally friendly is provided for synthesis of the 2-aminobenzothiazole compounds.

6-chloro-2-aminobenzothiazole derivative as well as preparation method and application thereof

The invention discloses a 6-chloro-2-aminobenzothiazole derivative as well as a preparation method and application thereof. The structure of the 6-chloro-2-aminobenzothiazole derivative is shown in a formula (I), wherein R is selected from substituted or

Synthesis of heteroleptic copper(I) complexes with phosphine-functionalized thiosemicarbazones: An efficient catalyst for regioselective N-alkylation reactions

Three new heteroleptic copper(I) complexes [Cu(PPh3)(PNS-H)] (1) (PNS-H?=?2-(2-(diphenylphosphino)benzylidene) thiosemicarbazone), [Cu(PPh3)(PNS-Me)] (2) (PNS-Me?=?2-(2-(diphenylphosphino)benzylidene)-4-methyl-3-thiosemicarbazone) and [Cu(PPh3)(PNS-Et)] (3) (PNS-Et?=?2-(2-(diphenylphosphino)benzylidene)-4-ethyl-3-thiosemicarbazone) have been synthesized and characterized by various spectral and analytical technique. The single-crystal X-ray diffraction study of complexes 2 and 3 confirmed the formation of complexes with Cu(I) ion, coordinated through P,N,S-donor atoms from the phosphino-thiosemicarbazone ligands. All the copper(I) complexes have been demonstrated as highly efficient catalysts for the synthesis of N-alkylated heterocyclic amine by the coupling of primary amines with alcohols at low catalyst loading, and the maximum yield was obtained up to 99%. The N-alkylation reactions were readily carried out under moderate conditions, and release of water was the only by-product. In addition, the effects of substituent's on the ligand, solvents, base and catalyst loading on the catalytic activity of the complexes have also been investigated. Advantageously, only one equivalent of the alcohol was consumed in the process.

Structure-dependent tautomerization induced catalyst-free autocatalyzed N-alkylation of heteroaryl amines with alcohols

Catalyst-free autocatalyzed dehydrative N-alkylation reactions of 2-aminobenzothiazoles, 2-aminopyrimidines, and 2-aminopyrazine with primary and secondary alcohols have been achieved for efficient, practical, and green synthesis of the versatile heteroaryl amine derivatives. These reactions were interestingly induced by structure-dependent tautomeric equilibria of the heteroaryl amines via MPV-O transfer hydrogenation of the imino tautomers by alcohols to give aldehydes as the key initiating step.

Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide

An efficient copper-catalyzed method for the synthesis of a variety of 2-aminobenzothiazoles has been developed. The reaction proceeded from carbodiimide and sodium hydrosulfide via a tandem reaction in the presence of copper(ii) trifluoromethanesulfonate to afford the corresponding 2-aminobenzothiazole derivatives in good to perfect yields. This journal is the Partner Organisations 2014.

Sodium hydroxide catalyzed N-alkylation of (hetero) aromatic primary amines and N1,C5-dialkylation of 4-phenyl-2-aminothiazoles with benzyl alcohols

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.

A straightforward synthesis of 2-aminobenzothiazoles from Herz compounds

2-Aminobenzothiazoles are readily synthesised from anilines, sulfur monochloride and isocyanides. The key step consists of an iodine-catalysed insertion of isocyanides into the S-S bond of hydrolysed Herz salts, with concomitant extrusion of sulfur monoxi

Regioselective N-alkylation of 2-aminobenzothiazoles with benzylic alcohols

The preparation of 2-(N-alkylamino)benzothiazoles via regioselecive N-alkylation of 2-aminobenzothiazoles has been accomplished by using benzylic alcohols as alkylating agents.