54013-55-7

Usage

Uses

Used in Organic Synthesis:
4,4-DIMETHYLOXAZOLIDINE-2-THIONE is used as a reagent in organic synthesis for its ability to react with various nucleophiles, making it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 4,4-DIMETHYLOXAZOLIDINE-2-THIONE is utilized as a precursor, contributing to the development of new drugs due to its unique chemical properties and reactivity.
Used in Research for Biological Activities:
4,4-DIMETHYLOXAZOLIDINE-2-THIONE is employed in research settings to explore its potential antimicrobial and anti-inflammatory properties, with the aim of discovering new therapeutic agents.
Used in Environmental and Toxicological Studies:
Due to its potential environmental impact and toxicity, 4,4-DIMETHYLOXAZOLIDINE-2-THIONE is also used in studies focused on understanding its effects on ecosystems and human health, which is crucial for establishing safe handling and disposal protocols.

InChI:InChI=1/C5H9NOS/c1-5(2)3-7-4(8)6-5/h3H2,1-2H3,(H,6,8)

Upstream product

• 124-68-5 2-Amino-2-methyl-1-propanol 
• 75-15-0 carbon disulfide 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 927-82-2 2-amino-2-methylpropyl hydrogensulfate 

Downstream Products

• 53244-69-2 2-benzylsulfanyl-4,4-dimethyl-4,5-dihydro-oxazole 
• 53244-68-1 2-(methylthio)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 100098-50-8 2-(3-bromobenzylthio)-4,4-dimethyl-2-oxazoline 
• 26654-39-7 4,4-dimethyl-1,3-oxazolidin-2-one 
• 100253-40-5 benzyl-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-amine 
• 58396-20-6 4,4-dimethyl-2-(1-phenyl-ethylsulfanyl)-4,5-dihydro-oxazole 
• 58396-22-8 2-(2-cyclohexyl-2-trimethylsilanyloxy-ethylsulfanyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 86064-95-1 4,4-dimethyl-2-(phenylthio)-4,5-dihydrooxazole 
• 89940-95-4 2-(2-Mercapto-ethylamino)-4,4-dimethyl-2-oxazolin 

Relevant academic research and scientific papers

New Synthetic Route to Tucatinib

A new and improved synthetic route to tucatinib is described that involves three key intermediates. The first of these, 4-([1,2,4]triazolo[1,5- a ]pyridin-7-yloxy)-3-methylaniline, was prepared on a 100 g scale in 33percent yield over five steps and 99percent purity. Next, N 4 -(4-([1,2,4]triazolo[1,5- a ]pyridin-7-yloxy)-3-methylphenyl)quinazoline-4,6-diamine was isolated in 67percent yield over three steps and >99percent purity. Then, 4,4-dimethyl-2-(methylthio)-4,5-dihydrooxazole trifluoromethanesulfonate was prepared under mild conditions in 67percent yield over two steps. Finally, tucatinib was obtained in 17percent yield over nine steps and in >99percent purity (HPLC). Purification methods used to isolate the product and the intermediates involved in the route are also reported.

An improved process for the preparation of 4,4-dimethyloxazolidine-2-thione

An improved process for the preparation of 4,4-dimethyloxazolidine-2-thione (1), an auxiliary used in the synthesis of (3S,4S)-[(R)-1′-((tert- butyldimethylsilyl)oxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone (2), a key intermediate for carbapenem synthesis is reported.

Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones

There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.

Thorpe-Ingold effect in the reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide

The Thorpe-Ingold effect is a key factor that affects the ring-closure rates and efficiency, as well as the structure of products in some ring-closure reactions. The reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide in the presence of potassium hydroxide produces the desired 4,4-disubstituted thiazolidine-2-thiones, and their isomers 5,5-disubstituted derivatives companying with their oxygen analogues 4,4-disubstituted oxazolidine-2-thiones. The formation of 5,5-disubstituted thiazolidine-2-thiones was rationalized via 2,2-disubstituted aziridine-1-carbodithioate intermediates, which were generated due to the Thorpe-Ingold effect. 4,4-Disubstituted oxazolidine-2-thiones were generated from carbon disulfide and free amino alcohols yielded via basic hydrolysis of active amino alcohol hydrogen sulfates in the reaction system.

Synthesis and use of achiral oxazolidine-2-thiones in selective preparation of trans 2,5-disubstituted tetrahydrofurans

The use of achiral N-acetyloxazolidine-2-thiones in the C-glycosylation of lactol acetates has allowed us to prepare with high diastereoselectivity the expected trans 2,5-disubstituted tetrahydrofurans. A study based on the role of the steric hindrance of the N-acetyloxazolidine-2-thiones is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.