2955-69-3

Usage

InChI:InChI=1/C9H11NS/c1-2-9(11)10-8-6-4-3-5-7-8/h3-7H,2H2,1H3,(H,10,11)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 79-03-8 propionyl chloride 
• 62-53-3 aniline 
• 340814-59-7 p-bromophenyl propanedithioate 
• 340814-58-6 p-chlorophenyl propanedithioate 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 2157-50-8 propiophenone oxime 
• 112933-66-1 p-tolyl propanedithioate 
• 88821-95-8 dithiopropanoate de phenyle 
• 98-09-9 benzenesulfonyl chloride 
• 859197-05-0 2-methyl-N-phenyl-3-thio-malonamic acid 

Downstream Products

• 80598-90-9 (E)-2-Methyl-hex-4-enethioic acid phenylamide 
• 82080-68-0 (2R,3S)-3-Hydroxy-2-methyl-N-phenyl-thiobutyramide 
• 82080-67-9 (2R,3R)-3-Hydroxy-2-methyl-N-phenyl-thiobutyramide 
• 80598-98-7 N-(methylthio-l propene-l yl) N-trimethylsilyl aniline 
• 53883-98-0 C₁₅H₁₄N₂O₂S₂ 
• 160917-37-3 6-Eth-(Z)-ylidene-2,5-diphenyl-2-trifluoromethyl-[1,3,5]thiadiazinan-4-one 
• 108228-64-4 [3-Methyl-5-methylene-dihydro-thiophen-(2E)-ylidene]-phenyl-amine 
• 108228-57-5 2-(N-acetyl-N-phenylamino)-3-methyl-5-methylthiophene 
• 86943-19-3 erythro-N-phenyl-2-methyl-3-<(trimethylsiloxy)methyl>thiopent-4-enamide 
• 86943-20-6 threo-N-phenyl-2-methyl-3-<(trimethylsiloxy)methyl>thiopent-4-enamide 
• 80598-91-0 4-Chloro-2-methyl-pent-4-enethioic acid phenylamide 
• 82080-81-7 Lithium; (Z)-1-(phenyl-trimethylsilanyl-amino)-propene-1-thiolate 
• 86943-17-1 erythro-N-phenyl-2-methyl-3-phenylthiopent-4-enamide 
• 82080-83-9 threo-N-phenyl-2,3-dimethylthio-4-pentenoylamide 

Relevant academic research and scientific papers

Structure-reactivity correlations in the aminolysis of aryl dithiomethyl- and dithiophenylacetates with anilines in acetonitrile

The kinetics and mechanism of the anilinolysis (XC6H4NH2) of dithio esters, RC(=S)SC6H4Z with R = C2H5 and C6H5CH2 are investigated in acetonitrile at 45.0 deg C. By application of various structure-reactivity correlations, selectivity parameters ρX, βX, ρZ, βZ and ρXZ are determined. The reactions are predicted to proceed stepwise with rate-limiting expulsion of the ArS- group. The dithio ester with R = C2H5 exhibits the fastest rate and the largest positive ρXZ value; this is interpreted to result from the strongest electron donating ability of the ethyl group in the intermediate and a crowded tetrahedral intermediate and transition state in which the nucleophile (X) and leaving group (Z) are in close proximity due to the bulky C2H5 group. Much faster rates are observed for the thiocarbonyl (C=S) rather than carbonyl (C=O) esters in the stepwise nucleophilic substitution reactions, which may be ascribed to the lower ?*C=S and ?*C-LG levels than those of the corresponding antibonding levels in the carbonyl esters. The normal kinetic isotope effects, kH/KD > 1.0, involving deuterated anilines suggest concurrent proton transfer with the expulsion of the ArS- leaving group in a four-center hydrogen bonded transition state.

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.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

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.