14204-31-0

Usage

Molecular Structure

The compound has a central isoindole ring with a 4-chlorophenylsulfanyl group attached to it.

Chemical Class

It falls under the class of isoindole-1,3-(2H)-dione derivatives.

Potential Applications

The compound has potential applications in the field of medicinal chemistry, particularly in the development of pharmaceuticals.

Unique Properties

The presence of sulfur and chlorine atoms in the molecule gives it unique chemical and biological properties, making it a subject of interest for further research and investigation.

Upstream product

• 136918-14-4 phthalimide 
• 106-54-7 p-Chlorothiophenol 
• 7764-30-9 2,2'-disulfanediylbis(isoindoline-1,3-dione) 
• 106-39-8 bromochlorobenzene 
• 54974-07-1 phthalimidesulfenyl chloride 
• 67207-21-0 p-chlorophenylsulfenyl bromide 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 2439-85-2 N-bromophthalimide 
• 1146-44-7 4,4'-dichlorophenyl thiosulfonate 

Downstream Products

• 1187616-39-2 ethyl 2-(4-chlorophenylthio)-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 
• 1416330-43-2 (R)-tert-butyl 3-(benzo[d][1,3]dioxol-5-ylmethyl)-3-((4-chlorophenyl)thio)-2-oxoindoline-1-carboxylate 
• 1416330-52-3 (R)3-(benzo[d][1,3]dioxol-5-ylmethyl)-3-((4-chlorophenyl)thio)indolin-2-one 
• 1416330-51-2 (R)-tert-butyl 3-((4-chlorophenyl)thio)-3-methyl-2-oxoindoline-1-carboxylate 
• 1615684-90-6 6-(2-(4-chlorophenylsulfanyl)pyrrol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole 
• 106119-12-4 4-morpholinyl p-chlorophenyl sulfide 
• 1393945-52-2 C₂₇H₂₆ClNO₃S 
• 1393945-51-1 C₂₅H₂₂ClNO₃S 
• 26760-21-4 methyl p-chlorobenzenesulphinate 
• 20168-75-6 1-(4-chlorophenyl)-2-(4-nitrophenyl)disulfane 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 110121-12-5 C₁₂H₈BrClS₂ 
• 33965-85-4 1-(4-chlorophenyl)-2-phenyldisulfane 
• 98-66-8 4-chloro-benzenesulfonic acid 

Relevant academic research and scientific papers

Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides

An efficient and eco-friendly electrochemical methodology for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols is presented. Various electron deficient N-acylsulfenamides are smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supports a possible free radical process and hydrogen is the only side product. This approach provides a safe, convenient, and economical preparation of synthetically important N-thiophthalimides on a gram scale.

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds

A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F).

Photochemical, Metal-Free Sigmatropic Rearrangement Reactions of Sulfur Ylides

Sigmatropic rearrangement reactions constitute one of the most fundamental reactions of carbenes. While state-of-the-art synthetic methods require the use of expensive precious metal catalysts, the application of visible light for the photolysis of α-aryldiazoacetates is much less investigated and provides an operationally simple entry to carbenes under mild reaction conditions. Herein, we report on blue-light induced sigmatropic rearrangement reactions of sulfur compounds with α-aryldiazoacetates. This process, depending on the substitution pattern of the sulfide, opens up formal insertion reactions of carbenes into S?N, S?C, or C?H bonds.

Benign synthesis of thiophosphates, thiophosphinates and selenophosphates in neat condition using N-chalcogenoimides as the source of electrophilic sulfur/selenium

A neat reaction protocol has been developed for synthesis of thiophosphate, thiophosphinate and selenophosphate compounds. N-chalcogenoimides have been used for chalcogenylation of P(O)H moieties of various H-phosphonates under solvent, catalyst and base free condition at room temperature in aerial atmosphere. Both S-aryl and S-alkyl phosphorothioate compounds were prepared by this method in good yields. Selenophosphates were also synthesized using N-(phenylseleno)phthalimide under solvent free condition.

Comparison of conventional and microwave-assisted synthesis of some new sulfenamides under free catalyst and ligand

Abstract: Sulfenamide and its derivatives (S–N bond) have been synthesized with classical method in the literature. However, microwave-assisted synthesis of a series of N-(substituted phenylthio), N-(benzylthio), N-(cyclothio), and N-(2-mercaptobenzimidazolyl)amines has been not in the literature yet. They have been obtained from treating some amines (4?mmol) with thiophthalimides (PhthSR, 1?mmol) using sulfur transfer reagent in the presence of 2-ethoxyethanol (β-ee, neat) under microwave irradiation at 50?°C. The scope of this reaction was shown by the efficient synthesis of sulfenamides in good to excellent yields of 70–98% under free catalyst and ligand. Nine of the synthesized sulfenamide derivatives are novel. All of the thiols react with morpholine to give corresponding sulfenamides in excellent yields of 78–98%. Thiophenol, 4-methylthiophenol, 4-chlorothiophenol, and 4-fluorothiophenol react with cyclohexylamine to give corresponding sulfenamides in high yields 81–92%. Thiophenol, 4-methylthiophenol, 4-chlorothiophenol react with pyrrolidine to give corresponding sulfenamides in good yields of 70–76%. We observed that the reaction of t-butylamine with N-(phenylthio)phthalimide gave desired sulfenamide under microwave irradiation in the presence of DPPH as radical scavenger reagent in high yield of 93%. Aniline, benzylamine, 1-hexylamine, ethanolamine, diethylamine, N-ethyl-n-butylamine, N-ethylaniline, N-benzylmethylamine, t-butylamine react with thiols to give symmetrical disulfides instead of desired products under microwave irradiation, 2-ethoxyethanol as a solvent (neat), and at 50?°C. In this study, microwave-assisted synthesis method was compared with the classical method. All the products obtained were purified with chromatographic method and the analysis of these products was confirmed with IR, 1H NMR, 13C NMR spectroscopy, MS spectrometry, and elemental methods. Graphical abstract: [Figure not available: see fulltext.].

The Rh(II)-catalyzed formal N-S bond insertion reaction of aryldiazoacetates into: N -phenyl-sulfenyl phthalimide

The Rh(ii)-catalyzed sulfur ylide [1,2]-rearrangement of carbenoids generated from aryldiazoacetates has been realized via N-S bond insertion, generating tertiary sulfides in moderate to excellent yields. This demonstrates the first use of the sulfur ylide [1,2]-rearrangement undergoing N-S bond insertion. This protocol could proceed smoothly with high regioselectivity, low catalyst loading (0.1 mol% Rh2(OAc)4), gram-scale reaction and broad substrate scope. And the product could be converted into glycine derivatives through simple procedures.

Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei

Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 μg/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure-activity relationship of the pyrrolobenzoxaboroles are also discussed.

The mechanisms of acid-catalyzed hydrolysis of n-(4-substituted arylthio) phthalimides

The acid-catalyzed hydrolysis of N-(4-substitutedarylthio)phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acids at 40.0 ±0.1° C. Analysis of the data by the excess acidity method, activation parameters, and substituent effects indicates hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.

The synthesis of sulfinylphthalimides and their reactions with some nucleophiles in dioxane

In this study, some N-(p-substituted-arylsulfinyl)phthalimides (1a-1e) were synthesized. The synthesized compounds were examined with respect to their substitution reactions with sodium ethoxide, sodium methoxide, methylamine, and t-butylamine in dioxane.

Preparation of 2-(2-cyanoethyl)sulfanyl-1H-isoindole-1,3-(2H)-dione and related sulfur-transfer agents

The title compound 3 and 4-[(2-cyanoethyl)sulfanyl]morpholine-3,5-dione 12 are both conveniently prepared in good yield from 2-cyanoethyl disulfide, which itself is readily prepared in one step from S-(2-cyanoethyl)isothiouronium chloride 4. In the same way, dimethyl and diphenyl disulfides are converted, into 2-methylsulfanyl- and 2-phenylsulfanyl-1H-isoindole-1,3-(2H)-diones 8a and 8b, respectively, also in good yields.