4686-01-5

Upstream product

• 56377-57-2 α-bromo-S-phenyl thioacetate 
• 62-53-3 aniline 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 103-71-9 phenyl isocyanate 
• 103-04-8 (phenylthio)acetic acid 
• 102-01-2 N-phenylacetoacetamide 
• 108-98-5 thiophenol 
• 134948-24-6 S-methyl α-(trimethylsilyl)ethanimidothioate 
• 134916-85-1 N-phenyl-(trimethylsilyl)ketenimine 
• 7031-27-8 (phenylthio)acetic acid chloride 
• 159223-63-9 syn-1-Phenyl-2-thiophenoxyethanone oxime 
• 197309-87-8 N-phenyl-2-trimethylsilyl-2-benzenesulfanyl-ethanimidoyl chloride 
• 197309-88-9 N-phenyl-trimethylsilyl(benzenesulfanyl)ketenimine 
• 227096-83-5 N-phenyl-benzenesulfanylketenimine 

Downstream Products

• 17530-97-1 N-phenyl-2-benzenesulfinylacetamide 
• 92249-42-8 N-Phenyl-2-phenylsulfanylethylamine 
• 16503-80-3 2,2-difluoro-N-phenyl-2-(phenylthio)acetamide 

Relevant academic research and scientific papers

Synthesis of acetamide derivatives using S-MWCNT and S-MC as an efficient heterogeneous catalysts

Sulphate modified multiwalled carbon nanotubes (S-MWCNT) and Mesoporous carbon (S-MC) catalysts were prepared by wet impregnation method. These materials were characterized by different analytical techniques such as Powder-XRD, BET surface area analysis, SEM-EDS and TEM analysis to evaluate their bulk and surface properties. Surface acidity of the catalyst was measured by TPD-NH3 technique, as well as n-butyl amine titration. The estimated surface acidity of S-MWCNT and S-MC using n-butyl amine titration was found to be 0.82 and 1.75 mmol/g respectively. The catalytic activity of these materials was investigated in the synthesis of acetamide derivatives using aromatic acids with substituted aromatic amines in a liquid phase reaction. The reaction conditions were optimized to achieve good % yield of the products. In general S-MC catalyst exhibited good catalytic activity and gave higher % yield of the respective acetamides than S-MWCNT. This is attributed to higher surface acidity of S-MC, however the catalyst was found to be non-recyclable. S-MWCNT exhibited moderate % yield and 100% selectivity towards the formation of products. S-MWCNT catalyst was recycled up to 5 times with a consistent % yield of the respective acetamide derivatives. The synthesized acetamide derivatives were analyzed by M.P, 1HNMR techniques.

Direct access to α-sulfenylated amides/esters: Via sequential oxidative sulfenylation and C-C bond cleavage of 3-oxobutyric amides/esters

An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.

Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids

A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.

Fluorination of sulfanyl amides using difluoroiodoarene reagents

A range of sulfur-containing amides have been fluorinated with the hypervalent iodine difluoride reagents 1, and two principal reaction pathways identified. Cephalosporin esters 2 having a heteroatom in the α-position to sulfur undergo fluorination in DCM with cleavage of the carbon-sulfur bond to form novel fluorinated β-lactams 4. Sulfides with electron-withdrawing groups in the α-position undergo α-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple α-phenylsulfanylacetamides 14-19. When β-hydrogens are present in the substrate a different route is followed, with deprotonation by basic fluoride taking place to yield vinyl sulfides 41-43. When an excess of the fluorinating reagent is used these vinyl sulfides can undergo further reaction in a novel tandem Pummerer-Additive-Pummerer process to yield α,β-difluoro sulfides 45-47.

Reactivity of N-phenyl silylated ketenimines with electrophilic reagents

We report the reactivity of new Cβ silylated ketenimines (4, 5, 6) and lithiated-silylated ketenimine 3 [easily generated from lithiated S-methyl- N-phenyl-trimethylsilylethanimidothioate 2] toward electrophilic reagents. Reactions of these ketenimines with strong electrophilic reagents such as sulfanyl chloride (PhSCl) gave access to new sulfanylated ketenimines. With less reactive species [benzenesulfinyl chloride (PhS(O)Cl), p-toluenesulfonyl chloride, trimethylhalosilanes, diisopropyl chlorophosphate, acetyl chloride and propylene oxide] and 3, the addition took place either on Cβ or on the nitrogen atom leading to relatively unstable functionalised ketenimines or new silylated ynamines respectively.

Dephosphonylation of β-carbonyl phosphonates

A new methodology has been developed for the P-C bond cleavage of β- carbonyl phosphonates. The α,α-disubstituted β-keto phosphonates and the α-carbamoyl phosphonates have been shown to undergo dephosphonylation by reaction of their lithium enolate with LiAlH4, followed by quenching with aqueous H2SO4, affording regioselectively α,α-disubstituted ketone and α-substituted and α,α-disubstituted secondary amides.

Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the S-terminus of coenzyme A and fragments.

The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction.Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters.The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase. Key words: spermidine, coenzyme A, cysteamine, β-aletheine, enzyme inhibitors.

Production of carbonyl compounds substituted in α-position

Production of carbonyl compounds substituted in the α-position and having the formula: EQU1 wherein R1 is alkyl, aralkyl, phenyl, toluyl, naphthyl, alkoxy or amino; R2 is hydrogen EQU2 A is hydrogen, alkyl, halo or EQU3 R6 is hydrogen or methyl, and R11 is alkyl; wherein said compounds are formed by reacting a sulfur ylide having the formula: EQU4 wherein Y is the radical EQU5 and R9 and R10 are alkyl or phenyl, with a solution containing both an electrophilic agent A' that is converted into the radical A and a nucleophilic agent B' that is converted into the radical B. The resulting carbonyl compounds are useful as starting materials for the production of paper, textile, and leather auxiliaries, plant protection agents, alkyd resins, polyesters and polyamides.