68055-34-5

Upstream product

• 100063-20-5 N-p-Thiotoluyl-succinimid 
• 100-46-9 benzylamine 
• 681440-55-1 4-methylthiobenzoic acid O-(4-nitrophenyl) ester 
• 104-87-0 4-methyl-benzaldehyde 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 865077-50-5 (1H-benzo[d][1,2,3]triazol-1-yl)(p-tolyl)methanethione 
• 5436-83-9 N-benzyl-4-methylbenzamide 
• 99-94-5 p-Toluic acid 

Downstream Products

• 5436-83-9 N-benzyl-4-methylbenzamide 

Relevant academic research and scientific papers

A multipathway coupled domino strategy: I2-mediated oxidative thionation for direct synthesis of thiobenzamides from miscellaneous substrates

An efficient iodine-mediated multipathway coupled domino reaction has been developed for the synthesis of thiobenzamides from benzylamines, benzylamines/aldehydes, and N-alkyl benzylamines under the same reaction conditions. This approach combines two consecutive domino processes in one pot using iodine as the oxidant.

Aminolysis of O-aryl thionobenzoates: Amine basicity combines with modulation of the nature of substituents in the leaving group and thionobenzoate moiety to control the reaction mechanism

(Chemical Equation Presented) A kinetic study is reported for aminolysis of O-Y-substituted phenyl thionobenzoates (la-f) and O-4-nitrophenyl X-substituted thionobenzoates (2a-f) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1°C. The reaction proceeds through one or two intermediates (i.e., a zwitterionic tetrahedral intermediate T± and its deprotonated form T-) depending on the basicity difference between the nucleophile and nucleofuge, that is, the reaction proceeds through T ± when the leaving aryloxide is less basic than the attacking amine, but through T± and T- when the leaving group is more basic than the amine. However, the reaction mechanism is not influenced by the electronic nature of the substituent X in the nonleaving group. The Hammett plot for the reactions of 2a-f with benzylamine is consisted of two intersecting straight lines, which might be interpreted as a change in the rate-determining step (RDS). However, the Yukawa-Tsuno plot for the same reactions exhibits an excellent linear correlation, indicating that the nonlinear Hammett plot is not due to a change in the RDS but caused by stabilization of the ground-state of the substrate through resonance interaction between the electron-donating substituent X and the thionocarbonyl moiety.

Benzotriazole-assisted thioacylation

Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/alkoxy-thioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.