5310-08-7

Usage

InChI:InChI=1/C26H22FNO6S3/c1-26(2)21(35)18(25-36-19(23(30)33-4)20(37-25)24(31)34-5)16-12-15(32-3)9-10-17(16)28(26)22(29)13-7-6-8-14(27)11-13/h6-12H,1-5H3

Upstream product

• 100-61-8 N-methylaniline 
• 5827-78-1 N-methyl-N-phenylpropanamide 
• 924-45-8 O-ethyl thiopropionate 

Downstream Products

• 111515-21-0 3-methyl-2-(N-methylanilino)naphtho<1,2-b>furan-5-ol 
• 111515-20-9 4,6-dichloro-3-methyl-2-(N-methylanilino)benzofuran-5-ol 
• 107611-11-0 5-chloro-2-ethylbenzo[d]thiazole 
• 111515-19-6 N-methyl-N-phenyl-1-(methylthio)prop-1-enylamine 

Relevant academic research and scientific papers

Contribution of Solvents to Geometrical Preference in the Z/ E Equilibrium of N-Phenylthioacetamide

We studied the Z/E preference of N-phenylthioacetamide (thioacetanilide) derivatives in various solvents by means of 1H NMR spectroscopy, as well as molecular dynamics (MD) and other computational analyses. Our experimental results indicate that the Z/E isomer preference of secondary (NH)thioamides of N-phenylthioacetamides shows substantial solvent dependency, whereas the corresponding amides do not show solvent dependency of the Z/E isomer ratios. Detailed study of the solvent effects based on molecular dynamics simulations revealed that there are two main modes of hydrogen (H)-bond formation between solvent and (NH)thioacetamide, which influence the Z/E isomer preference of (NH)thioamides. DFT calculations of NH-thioamide in the presence of one or two explicit solvent molecules in the continuum solvent model can effectively mimic the solvation by multiple solvent molecules surrounding the thioamide in MD simulations and shed light on the precise nature of the interactions between thioamide and solvent. Orbital interaction analysis showed that, counterintuitively, the Z/E preference of NH-thioacetamides is mainly determined by steric repulsion, while that of sterically congested N-methylthioacetamides is mainly determined by thioamide conjugation.

An efficient synthesis of benzothiazole using tetrabromomethane as a halogen bond donor catalyst

An efficient and mild protocol has been developed for the synthesis of 2-substituted benzothiazole under solvent- and metal-free conditions using CBr4 as the catalyst. This process involves the activation of a thioamide through halogen bond formation between the sulphur atom of the thioamide and bromine atom of the CBr4 molecule. The presence of halogen-bonding interaction between N-methylthioamides and tetrabromomethane has been demonstrated with several control experiments, spectroscopic analysis and density functional theory (DFT). This methodology has a wide substrate scope for the synthesis of both 2-alkyl and 2-aryl substituted benzothiazoles.