40800-69-9

Usage

Uses

Used in Pharmaceutical Research:
(3S)-3-(methylsulfanyl)-5-nitro-1,3-dihydro-2H-indol-2-one is used as a building block for the synthesis of various bioactive molecules due to its unique molecular structure and potential biological activities.
Used in Drug Development:
(3S)-3-(methylsulfanyl)-5-nitro-1,3-dihydro-2H-indol-2-one may be utilized in the development of new drugs, given its indolone core and functional groups that can be further modified to enhance its pharmacological properties.
Used in Chemical Research:
(3S)-3-(methylsulfanyl)-5-nitro-1,3-dihydro-2H-indol-2-one serves as a valuable tool in chemical research for understanding the reactivity and properties of indolone derivatives and their potential applications in various chemical processes.

Upstream product

• 22551-24-2 2-(methylthio)acetamide 
• 100-01-6 4-nitro-aniline 
• 4455-14-5 ethyl 2-(methylsulfinyl)acetate 

Relevant academic research and scientific papers

N-Chlorophthalimide as a mild and efficient chlorination reagent in the Gassman ortho alkylation of aromatic amines. Synthesis of 3-(methylthio)oxindoles

A practical modification of the Gassman 3-(methylthio)oxindole synthesis is reported. In our method, substituted anilines and 2-(methylthio)acetamide were reacted under mild reaction conditions, in the presence of N-chlorophthalimide as a chlorinating agent to give α-amidosulfides, which, in the next step of the process, were cyclized to give 3-(methylthio)oxindoles. The method was successfully applied for the synthesis of the key intermediate, 2-(2-amino-3-benzoylphenyl)-2-(methylthio)acetamide, in the process of the preparation of nepafenac, a commonly used ophthalmic drug.

A convenient modification of the Gassman oxindole synthesis

A modification of the Gassman oxindole synthesis is described that proceeds from anilines and ethyl (methylsulfinyl)acetate, using oxalyl chloride to activate the sulfoxide to facilitate the formation of the key N-S bonded intermediate. This procedure is particularly convenient for reactions carried out on smaller scales and for anilines that are susceptible to electrophilic halogenation.

Synthesis of oxindoles from anilines and β-thio carboxylic esters or amides

Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with β-thio esters or β-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thio-ether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thio-ether (aminocarbonyl) alkyl]aniline, reacting the orthosubstituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.

Process for preparing azasulfonium halide salts

Preparing azasulfonium halide salt derivatives of an aniline by reacting a halogen with a non-carbonylic dihydrocarbon sulfide, a beta-carbonylic hydrocarbon sulfide, or a β-thio ester or amide to form a halogen: sulfur compound complex and then reacting the complex with an aniline to form the azasulfonium halide salts. The azasulfonium halide salts are useful as intermediates in processes for making ortho-alkylated anilines, indoles, and 2-oxindoles which have a variety of known uses.