2682-49-7

Basic information

• Product Name: 1,3-THIAZOLIDIN-2-ONE
• Synonyms: 2-Thiazolidinone;Thiazolidine-2-one;1,3-THIAZOLIDIN-2-ONE;THIAZOLIDIN-2-ONE;1,3-Tetrahydro-2-thiazolone;1,3-THIAZOLIDINE-2-ONE;1,3-Thiazolan-2-one;2-Oxothiazolidine
• CAS NO: 2682-49-7
• Molecular Formula: C₃H₅NOS
• Molecular Weight: 103.14
• EINECS: 1312995-182-4
• Product Categories: API intermediates;agricultural chemical;plant growth modifier;fosthiazate;fungicide;lythidathion;pesticide
• Mol File: 2682-49-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 53-54℃
• Boiling Point: 160℃ (20 TORR)
• Flash Point: 103.5 °C
• Appearance: /
• Density: 1.277
• Vapor Pressure: 0.00414mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 12.78±0.20(Predicted)
• CAS DataBase Reference: 1,3-THIAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-THIAZOLIDIN-2-ONE(2682-49-7)
• EPA Substance Registry System: 1,3-THIAZOLIDIN-2-ONE(2682-49-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2682-49-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 2682-49-7 differently. You can refer to the following data:
1. lythidathion intermedia; agriculture intermedia;fosthiazate; lythidathion; fungicide;pesticide;plant growth modifier
2. 2-Thiazolidinone is used in the synthesis of (S)-4-iso-butylthiazolidin-2-one and (S)-4-benzylthiazolidin-2-one that show inhibitive activities against Candida albicans and Escherichia coli.

Synthesis Reference(s)

Tetrahedron Letters, 15, p. 2899, 1974 DOI: 10.1016/S0040-4039(01)91773-3

InChI:InChI=1/C3H5NOS/c5-3-4-1-2-6-3/h1-2H2,(H,4,5)

Synthetic route

carbon monoxide (201230-82-2) + Cysteamine (60-23-1) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With selenium; oxygen; acetonitrile	98%
Stage #1: carbon monoxide; Cysteamine With potassium carbonate; sulfur In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 4h; Stage #2: With oxygen In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 2h;	87%

2-mercaptoethylamine hydrochloride (156-57-0) + urea (57-13-6) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
at 180℃; for 3h; Temperature; Time; Concentration;	85%

carbon oxide sulfide (463-58-1) + 2-bromoethylamine hydrobromide (2576-47-8) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 1h;	80%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Cysteamine (60-23-1) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	78%

2-mercaptoethylamine hydrochloride (156-57-0) + 1,1'-carbonyldiimidazole (530-62-1) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
Stage #1: 2-mercaptoethylamine hydrochloride; 1,1'-carbonyldiimidazole With 18-crown-6 ether; potassium carbonate In acetonitrile for 18h; Heating; Stage #2: With water In acetonitrile for 4h; Heating; Further stages.;	68%
In ethanol for 15h; Ambient temperature;	63%
Stage #1: 2-mercaptoethylamine hydrochloride; 1,1'-carbonyldiimidazole With potassium carbonate; 18-crown-6 ether In acetonitrile at 80℃; for 19h; Heating / reflux; Stage #2: With sodium carbonate In water for 1h; Heating / reflux;	42%

thiazolidine-2-thione (134469-06-0) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With sodium; 2-bromoethanol In ethanol for 4h; Inert atmosphere; Reflux;	56%
With sodium ethanolate; 2-bromoethanol In ethanol at 60℃; for 4h;

thiazolidine-2-thione (134469-06-0) + 2-bromoethanol (540-51-2) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Inert atmosphere; Reflux;	56%

(2-mercapto-ethyl)-carbamic acid ethyl ester (88512-18-9) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With hydrotalcite; magnesium aluminum In toluene for 5h; Heating;	50%

dithiocarbonic acid S-(2-amino-ethyl ester)-S'-methyl ester; hydrochloride → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With sodium hydroxide

S-(2-aminoethyl)-S’-benzyldithiocarbonate hydrochloride (113511-38-9) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With sodium hydroxide

(4,5-dihydro-thiazol-2-yl)-nitroso-amine (3732-51-2) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With butan-1-ol

phosgene (75-44-5) + Cysteamine (60-23-1) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With toluene

S-(2-aminoethyl)-S’-benzyldithiocarbonate hydrochloride (113511-38-9) + aq.-ethanolic NaOH → thiazolidine-2-one (2682-49-7)

Cysteamine (60-23-1) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With selenium; CO; oxygen In tetrahydrofuran

CH2/TFA + glycine (56-40-6) → thiazolidine-2-one (2682-49-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In diethyl ether; benzene

thiazolidine-2-one (2682-49-7) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(2-oxothiazolidin-3-yl)acetate

Conditions	Yield
With potassium carbonate In acetonitrile for 2.5h; Reflux;	100%

thiazolidine-2-one (2682-49-7) + nickel (7440-02-0) → Ni(C3NS2H4)2 (28872-21-1, 158907-11-0)

Conditions	Yield
In acetonitrile byproducts: H2; Electrochem. Process; electrolyse of a soln. of the ligand in acetonitrile (NH4BF4) with a Nianode at room temp. under N2; filtered, washed with acetonitrile, dried in vac.; elem. anal.;	99%

thiazolidine-2-one (2682-49-7) + tetradeca-2,3-dienoic acid ethyl ester → C19H33NO3S

Conditions	Yield
With C29H30F6NOPS In 1,2-dichloro-ethane at 20℃; stereoselective reaction;	99%

thiazolidine-2-one (2682-49-7) + ethyl hexa-2,3-dienoate (131431-64-6, 113644-17-0) → C11H17NO3S

Conditions	Yield
With C29H30F6NOPS In 1,2-dichloro-ethane at 20℃; stereoselective reaction;	98%

thiazolidine-2-one (2682-49-7) + 2.9-dimethyl-1,10-phenanthroline (484-11-7) + nickel (7440-02-0) → Ni(C3NS2H4)2(C12N2H6(CH3)2)

Conditions	Yield
In acetonitrile byproducts: H2; Electrochem. Process; electrolyse of a soln. of the ligands in acetonitrile (NH4BF4) with a Ni anode at room temp. under N2; filtered, washed with acetonitrile, dried in vac.; elem. anal.;	96%

thiazolidine-2-one (2682-49-7) + (±)-ethyl 6-phenylhexa-2,3-dienoate (1422199-48-1) → C17H21NO3S

Conditions	Yield
With C29H30F6NOPS In 1,2-dichloro-ethane at 20℃; stereoselective reaction;	95%

thiazolidine-2-one (2682-49-7) + C11H16O4 (1286277-95-9) → C14H21NO5S

Conditions	Yield
With C29H30F6NOPS In 1,2-dichloro-ethane at 20℃; stereoselective reaction;	95%

thiazolidine-2-one (2682-49-7) + 2,6-Dichloropyrimidine (3934-20-1) → 3-(2-chloropyrimidin-4-yl)thiazolidin-2-one

Conditions	Yield
With sodium methansulfinate; tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran at 50℃; for 5h; Green chemistry; regioselective reaction;	93%

thiazolidine-2-one (2682-49-7) + (±)-ethyl hepta-2,3-dienoate (861668-05-5) → C12H19NO3S

Conditions	Yield
With C29H30F6NOPS In 1,2-dichloro-ethane at 20℃; stereoselective reaction;	93%

thiazolidine-2-one (2682-49-7) + ethyl γ-isopropyl allenoate (235742-76-4) → C12H19NO3S

Conditions	Yield
With C29H30F6NOPS In 1,2-dichloro-ethane at 20℃; stereoselective reaction;	85%

thiazolidine-2-one (2682-49-7) + 5-chloro-1-methyl-4-nitroimidazole (4897-25-0) → 3-(3-Methyl-5-nitro-3H-imidazol-4-yl)-thiazolidin-2-one (86230-97-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 15 - 100℃; for 2.25h;	83%

thiazolidine-2-one (2682-49-7) + phenylacetaldehyde (122-78-1) → (E)-3-styrylthiazolidin-2-one

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene at 130℃; for 6h; Inert atmosphere; Molecular sieve;	78%

thiazolidine-2-one (2682-49-7) → 3-nitrosothiazolidin-2-one

Conditions	Yield
With 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide; trifluoroacetic acid In acetonitrile at 20℃; Sealed tube;	78%

thiazolidine-2-one (2682-49-7) + 2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7) → 3-(N-phthaloyl-3-aminopropyl)thiazolidin-2-one

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 16h; Heating;	72%
With potassium carbonate; 18-crown-6 ether In acetonitrile for 17h; Heating / reflux;	55%

thiazolidine-2-one (2682-49-7) + ibuprofen (15687-27-1) → 3-(2-(4-isobutylphenyl)propanoyl)thiazolidin-2-one

Conditions	Yield
Stage #1: ibuprofen With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.333333h; Stage #2: thiazolidine-2-one In dichloromethane at 20℃; for 4h;	70%

thiazolidine-2-one (2682-49-7) + 2-(2-((2-(4-((t-Boc)amino)phenyl)quinolin-6-yl)oxy)ethoxy)ethyl 4-methylbenzenesulfonate → t-butyl (4-(6-(2-(2-(2-oxothiazolidin-3-yl)ethoxy)ethoxy)quinolin-2-yl)phenyl)carbamate

Conditions	Yield
With lithium oxide Microwave irradiation;	70%

thiazolidine-2-one (2682-49-7) + (S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid (79640-70-3) → tert-butyl (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxo-5-(2-oxothiazolidin-3-yl)pentanoate

Conditions	Yield
Stage #1: (S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: thiazolidine-2-one In N,N-dimethyl-formamide for 16h;	65%
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 16h;	42%

thiazolidine-2-one (2682-49-7) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → C12H14BrNO3S (1018331-29-7)

Conditions	Yield
Stage #1: thiazolidine-2-one With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In tetrahydrofuran Reflux; Inert atmosphere;	63%

thiazolidine-2-one (2682-49-7) + 2,3-dimethoxy-6-bromobenzyl bromide (175844-54-9) → C12H14BrNO3S (1018331-30-0)

Conditions	Yield
Stage #1: thiazolidine-2-one With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 6-bromo-2,3-dimethoxybenzyl bromide In tetrahydrofuran Reflux; Inert atmosphere;	61%

thiazolidine-2-one (2682-49-7) + Dimethyl-p-toluidine (99-97-8) → C12H16N2OS

Conditions	Yield
With tetrabutyl ammonium fluoride; acetic acid In acetonitrile at 60℃; for 3h; Electrochemical reaction; Inert atmosphere;	59%

thiazolidine-2-one (2682-49-7) + 2,2′-(naphthalene-1,4-diylbis(((4-methoxyphenyl)sulfonyl)azanediyl))diacetic acid (1567836-15-0) → N,N'-(naphthalene-1,4-diyl)bis(4-methoxy-N-(2-oxo-2-(2-oxothiazolidin-3-yl)ethyl)benzenesulfonamide)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide	58%
Stage #1: 2,2′-(naphthalene-1,4-diylbis(((4-methoxyphenyl)sulfonyl)azanediyl))diacetic acid With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: thiazolidine-2-one In N,N-dimethyl-formamide	0.368 g

thiazolidine-2-one (2682-49-7) → 2,4-dibromo-1,3-thiazole (4175-77-3)

Conditions	Yield
With phosphorus(V) oxybromide at 110℃; for 3h;	57%

thiazolidine-2-one (2682-49-7) + 2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5) → C10H18N2O3S

Conditions	Yield
Stage #1: thiazolidine-2-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: 2-(tert-butoxycarbonylamino)ethyl bromide In N,N-dimethyl-formamide at 20℃; for 2h;	51%

Upstream product

• 113511-38-9 S-(2-aminoethyl)-S’-benzyldithiocarbonate hydrochloride 
• 3732-51-2 (4,5-dihydro-thiazol-2-yl)-nitroso-amine 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 60-23-1 Cysteamine 
• 134469-06-0 thiazolidine-2-thione 
• 56-40-6 glycine 
• 88512-18-9 (2-mercapto-ethyl)-carbamic acid ethyl ester 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 201230-82-2 carbon monoxide 
• 57-13-6 urea 
• 75-44-5 phosgene 
• 540-51-2 2-bromoethanol 
• 463-58-1 carbon oxide sulfide 

Downstream Products

• 127881-45-2 (4-Benzothiazol-2-yl-benzyl)-(2-oxo-thiazolidin-3-yl)-phosphinic acid ethyl ester 
• 4175-77-3 2,4-dibromo-1,3-thiazole 
• 1018331-29-7 C₁₂H₁₄BrNO₃S 
• 1018331-30-0 C₁₂H₁₄BrNO₃S 

Relevant articles and documents

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Thiazolidine prodrugs as protective agents against γ-radiation-induced toxicity and mutagenesis in V79 cells

Representatives of two classes of thiazolidine prodrug forms of the well-known radioprotective agents L-cysteine, cysteamine, and 2-[(aminopropyl)amino]ethanethiol (WR-1065) were synthesized by condensing the parent thiolamine with an appropriate carbonyl donor. Inherent toxicity of the prodrugs was assessed in V79 cells using a clonogenic survival assay. Protection against radiation-induced cell death was measured similarly after exposure to 0-8 Gy γ (137Cs) radiation. Antimutagenic activity was determined at the hypoxanthine-guanine phosphoribosyltransferase (HGPRT) locus. All thiazolidine prodrugs exhibited less toxicity than their parent thiolamines, sometimes dramatically so. Protection against radiation-induced cell death was observed for the 2-alkylthiazolidine, 2(R,S)-D-ribo-(1′,2′,3′,4′-tetrahydroxybutyl) thiazolidine (RibCyst), which produced a protection factor at 8 Gy of 1.8; the cysteine analogue, 2(R,S)-D-ribo-(1′,2′,3′,4′-tetrahydroxybutyl) thiazolidine-4(R)-carboxylic acid (RibCys), was less active. RibCyst also exhibited excellent antimutational activity, rivaling that of WR-1065. The 2-oxothiazolidine analogues showed little activity in either determination under the conditions tested, perhaps due to their enhanced chemical and biochemical stability.

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