1438-45-5

Usage

InChI:InChI=1/C9H14N2S/c1-2-4-8(5-3-1)11-9-10-6-7-12-9/h6-8H,1-5H2,(H,10,11)

Upstream product

• 3034-52-4 2-chlorothiazole 
• 108-91-8 cyclohexylamine 
• 96-50-4 2-thiazolylamine 
• 108-94-1 cyclohexanone 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 107-20-0 2-chloroethanal 
• 5055-72-1 N-cyclohexylthiourea 
• 1122-82-3 isothiocyanatocyclohexane 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 108-93-0 cyclohexanol 

Downstream Products

• 1222926-94-4 1-(1,3-benzothiazol-2-yl)-1-[2-(cyclohexylamino)-1,3-thiazol-5-yl]-2,2,2-trifluoroethanol 
• 637042-53-6 C₂₈H₂₅ClF₃N₃O₃S 
• 637042-49-0 C₂₈H₂₈ClN₃O₃S 

Relevant academic research and scientific papers

Synthetic method for N-alkyl(benzo)thiazole

The invention provides a synthetic method for N-alkyl(benzo)thiazole. The synthetic method comprises the following steps: putting 0.4-0.8 mmol of a carbonyl compound, 0.4-0.8 mmol of p-toluenesulfonylhydrazide and 4-10 mL of a solvent in a flask and carrying out a reaction at 30 DEG C to 80 DEG C for 1 to 3 h; adding 0.4 mmol of 2-aminothiazole, 0.4-0.8 mmol of metal copper salt and 0.4-1.2 mmolof an alkali substance into the above reaction system, carrying out heating to 100 DEG C to 150 DEG C, and continuing the reaction for 2 h to 5 h; terminating the reaction to obtain a reaction productA; and subjecting the product A to purification and impurity separation so as to obtain pure N-alkyl(benzo)thiazole. According to the invention, the intermediate sulfonyl hydrazone is prepared from the carbonyl compound and sulfonyl hydrazide, and reacts with a 2-aminothiazole substance in the presence of a catalyst and under alkali conditions to obtain N-alkyl(benzo)thiazole. The synthetic method of the invention has the advantages of simple operation, low cost, high product yield and wide application range of a substrate. At the same time, the established method can also realize the synthesis of the anti-inflammatory drug fanetizole, and thus has high practical value.

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles

An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.

Pd-PEPPSI-IPentAn Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions

We report herein a highly efficient Pd-catalyzed amination by "bulky-yet-flexible" Pd-PEPPSI-IPentAn complexes. The relationship between the N-heterocyclic carbenes (NHCs) structure and catalytic properties was discussed. Sterically hindered (hetero)aryl chlorides and a variety of aliphatic and aromatic amines can be applied in this cross-coupling, which smoothly proceeded to provide desired products. The operationally simple protocol highlights the rapid access to CAr-N bond formation under mild conditions without the exclusion of air and moisture.