39203-76-4

Upstream product

• 6852-54-6 N-(benzylidene)ethylamine 
• 14321-27-8 N-ethylbenzylamine 
• 150-60-7 dibenzyl disulphide 
• 75-04-7 ethylamine 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 100-47-0 benzonitrile 
• 13522-38-8 thiobenzoic acid O-(4-nitrophenyl) ester 
• 942-96-1 O-butyl benzothioate 
• 108-86-1 bromobenzene 
• 542-85-8 Ethyl isothiocyanate 
• 100-52-7 benzaldehyde 
• 30931-22-7 thiobenzoic acid O-(4-acetylphenyl) ester 
• 30924-75-5 thiobenzoic acid O-p-tolyl ester 

Downstream Products

• 70015-12-2 N-ethyl-thiobenzimidic acid methyl ester 
• 88295-99-2 2-Ethyl-4-methyl-1-phenyl-6-thia-2-azabicyclo<2.2.0>hexan-3-one 
• 88295-99-2 (1R,4S)-6-Ethyl-4-methyl-1-phenyl-2-thia-6-aza-bicyclo[2.2.0]hexan-5-one 

Relevant academic research and scientific papers

Ynamide-Mediated Thioamide and Primary Thioamide Syntheses

Environmentally friendly ynamide-mediated thioamidation of monothiocarboxylic acids with amines or ammonium hydroxide for the syntheses of thioamides and primary thioamides is described. Simple and mild reaction conditions enable the reaction to tolerate a wide variety of functional groups such as hydroxyl group, ester, tertiary amine, ketone, and amide moieties. Readily available NaSH served as the sulfur source, avoiding the use of toxic, expensive, and malodorous organic sulfur reagents and making this strategy environmentally friendly and practical. Importantly, the stereochemical integrity of α-chiral monothiocarboxylic acids was maintained during the activation step and subsequent aminolysis process, thus offering a racemization-free strategy for peptide C-terminal modification. Furthermore, a number of thioamide-modified drugs were prepared in good yields by using this protocol and the synthesized primary thioamides were transformed into backbone thiazolyl modified peptides.

An efficient and straightforward approach for accessing thionoesters: Via palladium-catalyzed C-N cleavage of thioamides

We report for the first time the coupling of activated thioamides with alcohols to efficiently form thionoesters via a palladium-catalyzed C-N cleavage strategy. The new approach employs thioamides as a thioacylating reagent to give thionoesters in moderate to good yields. Notably, this methodology demonstrates a broad substrate scope, as alkyl/aryl alcohols are well tolerated, and this process might facilitate the synthesis of sulfur-containing compounds under simple and mild conditions. This journal is

Microwave-Assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines: A rapid and efficient protocol for thioamides

An efficient protocol for synthesis of thioamides was developed via the microwave-Assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines. This process is scalable and tolerates a wide spectrum of amines to deliver the corresponding products in moderate to excellent yields in 10 minutes, providing a cheap and rapid approach to thioamides.

Synthesis of benzo[c]thiophen-1(3h)-imine and 2,3-dihydro-1h-isoindole-1-thione derivatives through cyclizations of 2-(1-hydroxyalkyl)benzothioamides

The reaction of N-alkyl-2,N-dilithiobenzothioamides, generated by treating N-alkylbenzothioamides with two equivalents of butyllithium, with aldehydes gives the corresponding 2-(1-hydroxyalkyl)benzothioamides, which undergo cyclization on treatment with m

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.

Synthesis of thioamides by catalyst-free three-component reactions in water

Three-component reactions involving amines, aldehydes, and elemental sulfur powder are reported to afford thioamides in a simple one-pot procedure in the absence of a catalyst. A variety of thioamides can be obtained in good to excellent yields up to 88 %. Three-component reactions involving amines, aldehydes, and sulfur powder afford thioamides in a simple one-pot procedure. A variety of substituted thioamides are obtained in good to excellent yields up to 88 %. Copyright

Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid

A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.

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.

Effect of amine nature on reaction mechanism: Aminolyses of O-4-nitrophenyl thionobenzoate with primary and secondary amines

Pseudo-first-order rate constants (kobs) have been measured spectrophotometrically for reactions of O-4-nitrophenyl thionobenzoate (2) with a series of primary and acyclic secondary amines. The plots of kobs vs amine concentration are linear for the reaction of 2 with primary amines. The slope of the Bronsted-type plot for the reaction of 2 with primary amines decreases from 0.77 to 0.17 as the amine basicity increases, indicating that the reaction proceeds through a zwitterionic addition intermediate in which the rate-determining step changes from the breakdown of the intermediate to the reaction products to the formation of the intermediate as the amine basicity increases. On the other hand, for reactions with all the acyclic secondary amines studied, the plot of kobs vs amine concentration exhibits an upward curvature, suggesting that the reaction proceeds through two intermediates, e.g., a zwitterionic addition intermediate and an anionic intermediate. The microscopic rate constants (k1, k-1, k2, and k3 where available) have been determined for the reactions of 2 with all the primary and secondary amines studied. The k1 value is larger for the reaction with the primary amine than for the reaction with the isobasic acyclic secondary amines, while the k-1 value is much larger for the latter reaction than for the former reaction. The k3 value for the reaction with secondary amine is independent of the amine basicity. The small k2/k-1 ratio is proposed to be responsible for the deprotonation process observed in aminolyses of carbonyl or thiocarbonyl derivatives.