5310-17-8

Usage

InChI:InChI=1/C9H11NS/c1-7-3-5-9(6-4-7)10-8(2)11/h3-6H,1-2H3,(H,10,11)

Upstream product

• 5132-17-2 N,N'-di(p-tolyl)acetamidine 
• 106-49-0 p-toluidine 
• 62-55-5 thioacetamide 
• 122-00-9 para-methylacetophenone 
• 2089-33-0 4-methylacethophenone oxime 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 540-23-8 p-toluidine hydrochloride 
• 5816-98-8 ethyl 2-((4-methylphenyl)carbamothioyl)-3-oxobutanoate 
• 14277-01-1 N-(4-methylphenyl)acetamidine 
• 193765-64-9 4-bromophenyl dithioacetate 
• 193765-63-8 4-chlorophenyl dithioacetate 
• 193765-62-7 4-methylphenyl dithioacetate 
• 36797-15-6 phenyl dithioacetate 
• 926-67-0 O-Ethyl thioacetate 

Downstream Products

• 40746-60-9 5-methyl-1-(4-methylphenyl)-1H-tetrazole 
• 5132-17-2 N,N'-di(p-tolyl)acetamidine 
• 103-89-9 4-Methylacetanilide 
• 2941-71-1 2,6-dimethylbenzothiazole 

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.

Evaluation of dipole moment and electrophilicity on the nature of click-type coupling reaction between thioamide and sulfonyl azide

A cooperated experimental and computational investigation on sulfonyl amidine formation from thioamides and sulfonyl azides is described. The data support a non-concerted two-step pathway for the coupling reaction and also indicate that dipole moment of t

Transamidation of thioacetamide catalyzed by SbCl3

A transamidation reaction of thioacetamide with primary and secondary amines is described. The use of catalytic amounts of SbCl3 notably increases the yields and diminishes the reaction times. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. This is one of the few examples where antimony has been used as a catalyst in organic reactions.

O,O-Diethyl dithiophosphoric acid mediated direct synthesis of thioamides from aldehydes and ketones

A general and convenient method for a one-pot conversion of aldehydes and ketones into thioamides has been developed. The protocol involves oximation of aldehydes and ketones followed by deoxygenative thioamidation of oximes with O,O-diethyl dithiophosphoric acid which acts as an acid as well a source of sulfur. The method is operationally simple, high yielding, and also applicable to the conversion of amides and nitriles into the corresponding thioamides.

Facile synthesis of thioamides via P2S5-mediated beckmann rearrangement of oximes

A facile and efficient approach to the synthesis of secondary thioamides from ketoximes via Beckmann rearrangement has been established, using phosphorus pentasulfide as a dehydrating and thiating agent. It is also efficient for the preparation of primary thiobenzamide from benzaldoxime. This approach features simple-operation, easy-control and good to excellent yields.

Facile and odorless one-pot process for the synthesis of N-substituted thioamides via TsCl-mediated Beckmann rearrangement of ketoximes

A facile and odorless one-pot thionation process for the synthesis of N-substituted thioamides using chemically stable and inexpensive thiourea reagent via the Beckmann rearrangement of ketoximes, has been described. Georg Thieme Verlag Stuttgart · New York.

Ketoximes to N-substituted thioamides via PSCl3 mediated Beckmann rearrangement

N-Substituted thioamides were accessed from ketoximes by utilising PSCl3 as a uniquely capable reagent to induce Beckmann rearrangement as well as to capture the intermediate nitrilium ion. The Royal Society of Chemistry 2009.

Kinetics and Mechanism of the Aminolysis of Phenyl Dithioacetates in Acetonitrile

The aminolysis reactions of phenyl dithioacetates with anilines (AN), N,N-dimethylanilines (DMA), and benzylamines (BA) in acetonitrile are investigated. The mechanism is relatively simple, involving a zwitterionic tetrahedral intermediate, T±, and is uncomplicated by the fast proton transfer step which may become rate limiting in the aminolysis of thiono and dithio esters and carbonates with poor leaving groups in water. The mechanism changes from rate-limiting expulsion of the leaving group with βX = 0.80-0.86 and βZ = -0.71 to -0.84 for ANs and DMAs to rate-limiting attack by the nucleophile with much smaller magnitudes of βX and βZ for BAs. The relatively large βXZ values for the former series and a smaller βXZ for the latter series support the proposed mechanistic change.