158554-93-9

Basic information

• Product Name: 3-benzyl-4-isopropyl-1,3-thiazolidin-2-one 1,1-dioxide
• Synonyms: 3-benzyl-4-isopropyl-1,3-thiazolidin-2-one 1,1-dioxide
• CAS NO: 158554-93-9
• Molecular Formula: C13H17NO3S
• Molecular Weight: 267.34398
• Mol File: 158554-93-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-benzyl-4-isopropyl-1,3-thiazolidin-2-one 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-4-isopropyl-1,3-thiazolidin-2-one 1,1-dioxide(158554-93-9)
• EPA Substance Registry System: 3-benzyl-4-isopropyl-1,3-thiazolidin-2-one 1,1-dioxide(158554-93-9)

Safety Data

• Hazardous Substances Data: 158554-93-9(Hazardous Substances Data)

Upstream product

• 158554-90-6 (S)-3-Benzyl-4-isopropyl-thiazolidine-2-thione 

Relevant articles and documents

Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides

Four examples of the chiral thiazolidin-2-one 1,1-dioxides 5 have been prepared by reaction of the appropriate amino alcohols 11 with CS2 in aqueous sodium hydroxide to give the thiazolidine-2-thiones 12, followed by oxidation with KMnO4 under phase-transfer conditions in the presence of benzoic acid, either directly or via the thiazolidin-2-ones 13. Upon flash vacuum pyrolysis (FVP) at 650°C, 5a-c decompose mainly by loss of SO2 to give an alkene and benzyl isocyanate together with other products from fragmentation of the N-benzyl group. A significant minor pathway involves net loss of CO2 and water to give the 2-phenyl-4,5-dihydrothiazoles 21 together with their aromatisation products 22 and 23. A mechanism for this new heterocyclic transformation is proposed involving initial expansion to a cyclic carbamic-sulnnic anhydride (2,1,4-oxathiazin-3-one 1-oxide). The fully assigned 13C NMR spectra are presented for 5, 12 and 13 and the 33S NMR spectrum has been obtained for 5c.

Unexpected Thermal Extrusion of CO2 from 3-Benzylthiazolidin-2-one 1,1-Dioxides to Give 2-Phenylthiazolines and Thiazoles

Flash vacuum pyrolysis of a series of chiral 3-benzylthiazolidin-2-one 1,1-dioxides 5, readily prepared from amino acids, results mainly in loss of SO2 to give an alkene and benzyl isocyanate, but a significant minor pathway involves unexpected loss of CO2 and water to give 2-phenylthiazolines 13 and derived thiazoles.