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Quality Control of 2,4-Thiazolidinedione Purity: 97% SDS Specification

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Product Details of 2,4-Thiazolidinedione

CAS No. :	2295-31-0
Formula :	C₃H₃NO₂S
M.W :	117.13
SMILES Code :	O=C1SCC(N1)=O
Synonyms :	Thiazolidinedione
MDL No. :	MFCD00005478
InChI Key :	ZOBPZXTWZATXDG-UHFFFAOYSA-N
Pubchem ID :	5437

Safety of 2,4-Thiazolidinedione

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 2,4-Thiazolidinedione

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2295-31-0 ]

[ 2295-31-0 ] Synthesis Path-Downstream 1~26

1
[ 13959-34-7 ]
[ 2295-31-0 ]
[ 32594-62-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1971,vol. 7,p. 559 - 560.
Khimiya Geterotsiklicheskikh Soedinenii,1971,vol. 7,p. 599 - 600.

2
[ 2295-31-0 ]
[ 37785-48-1 ]
[ 86106-22-1 ]

References: [1]Tetrahedron,1982,vol. 38,p. 3255 - 3266.

3
[ 7732-18-5 ]
[ 2192-06-5 ]
[ 2295-31-0 ]
[ 7664-41-7 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1874,vol. <2>9,p. 29.

4
[ 294886-88-7 ]
[ 2295-31-0 ]
[ 6142-15-0 ]

References: [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 569 - 575.

5
[ 2295-31-0 ]
[ 28090-12-2 ]
5-[4-(3-methyl-but-2-enyloxy)-benzylidene]-thiazolidine-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1149 - 1154.

6
[ 2295-31-0 ]
2,4-dichloro-thiazol-4-yl-carboaldehyde [ No CAS ]
[ 104146-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; trichlorophosphate; In N-methyl-acetamide; dichloromethane; 1,2-dichloro-ethane;	REFERENCE EXAMPLE 4 Production of 2,4-dichloro-thiazol-4-yl-carboaldehyde of the formula STR22 To a solution of dimethylformamide (73.1 g) in dichloroethylene (200 ml) was added dropwise phosphorus oxychloride (122.7 g) under ice-cooling, followed by stirring for 30 minutes (for preparation of Vilsmeier reagent). The resultant solution was admixed with thiazolin-2,4-dione (23.4 g) and heated for 1 hour under refluxing. The reaction solution obtained was cooled to ambient temperature, poured onto ice (200 g), neutralized by addition of sodium acetate and then extracted 3 times with 200 ml-portions of methylene chloride. The resultant extract in methylene chloride was washed with a small volume of saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue obtained was purified chromatographically on a column of silica-gel as developed with benzene-ethyl acetate (10:1) as eluent. 4-Chloro-thiazol-5-yl-carboaldehyde (0.34 g) was afforded, and the titled compound (2.05 g) was also obtained as light yellow colored crystals. NMR, delta (CDCl3): 9.90 (1H, s) MS (m/e): 182 (M+ +1)

References: [1]Patent: US4839350,1989,A .

7
[ 2295-31-0 ]
[ 104146-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; trichlorophosphate; In N-methyl-acetamide; dichloromethane;	REFERENCE EXAMPLE 3 Production of 4-chloro-thiazol-5-yl-carboaldehyde of the formula STR20 Phosphorus oxychloride (122.7 g) was added dropwise to dimethylformamide (73.1 g) under ice-cooling, and the mixture obtained was stirred for 30 minutes (for preparation of Vilsmeier reagent). The mixture was then admixed with thiazoline-2,4-dione STR21 (23.4 g), followed by heating at 100° C. for 3 hours. The reaction solution was cooled to ambient temperature, poured onto ice (200 g), neutralized by addition of sodium acetate and then extracted 4 times with 200 ml-portions of methylene chloride. The resultant extract in methylene chloride was washed with a small volume of saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified chromatographically on a column of silica gel as developed with benzene-ethyl acetate (10:1) as eluent. The titled compound (1.10 g) was obtained as light yellow colored crystals. NMR, delta (CDCl3): 8.93 (1H, d, J=1 Hz), 10.03 (1H, d, J=1 Hz). MS (m/e): 148 (M+ +1)

References: [1]Patent: US4839350,1989,A .

8
[ 2295-31-0 ]
[ 328125-41-3 ]
[ 171663-13-1 ]
tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(a) tert-Butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]carbamate In a manner similar to that of Example 1(f) by reacting 7.4 g (24 mmol) of tert-butyl (4'-formyl-biphenyl-3-ylmethyl)carbamate (prepared as in Example 1(e) from tert-butyl (3-bromo benzyl)carbamate)with 2.8 g (24 mmol) of 2,4-thiazolidine dione, 9 g (95%) of the expected product are obtained.

References: [1]Patent: US2004/39038,2004,A1 .

9
[ 2295-31-0 ]
[ 42059-80-3 ]
[ 1093128-14-3 ]

References: [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 2412 - 2417.

10
[ 2295-31-0 ]
[ 56442-17-2 ]
[ 1055977-81-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6161 - 6165.

11
[ 2295-31-0 ]
[ 27143-07-3 ]
[ 1049122-22-6 ]

References: [1]Synthesis,2011,p. 1799 - 1803.

12
[ 2295-31-0 ]
[ 10102-94-0 ]
[ 1421592-33-7 ]

References: [1]Asian Journal of Chemistry,2013,vol. 25,p. 1661 - 1665.

13
[ 2295-31-0 ]
[ 204205-33-4 ]
[ 1563931-94-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 6h;	A mixture of 1,3-thiazolidine-2,4-dione (6, 1 mmol),<strong>[204205-33-4]2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone</strong> (7, 1 mmol) and sodium bicarbonate (2 equiv) were dissolved in DMF and stirred atambient temperature for 6 h. After completion of the reaction as evidenced by TLC (eluent 7:3 / hexane:ethyl acetate) the reaction mixture was poured into water (25 mL), extracted with ethyl aceate and the solvent distilled under vacuum to obtain pure 8.

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1089 - 1093.

14
[ 2295-31-0 ]
[ 10102-94-0 ]
[ 1494469-67-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrabutylammonium acetate; at 100℃;	General procedure: A mixture of 1 (0.735 g, 5 mmol) and 2/4 (5 mmol) were added in succession insingle lots to the TBAA melt, and the reaction mixture was heated at 100 C andmaintained for 15-20 min. On completion of the reaction, as monitored by TLC,the reaction mixture was cooled to room temperature; ethanol was added to thereaction mixture and was refluxed for 5 min to extract the ionic liquid into ethanol.After cooling to room temperature, the separated product (3/5) was filtered off andwashed with ethanol (2-3 ml) to afford pure 3/5 as insoluble product. The ethanolwas evaporated to recover TBAA, which could be reused at least four times withoutloss of activity.

References: [1]Synthetic Communications,2014,vol. 44,p. 368 - 373.

15
[ 2295-31-0 ]
[ 51264-76-7 ]
C₁₄H₁₃NO₆S [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2014,vol. 87,p. 175 - 185.
[2]Archiv der Pharmazie,2015,vol. 348,p. 421 - 432.

16
[ 2295-31-0 ]
[ 14651-42-4 ]
3-((adamantan-1-yl)methyl)thiazolidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: The compounds were prepared according to the procedure previouslydescribed.19,30 To a refluxing solution of thiazolidine-2,4-dione (43 mmol) in ethanol (25 mL) was added a hot solutionof potassium hydroxide (45 mmol) in ethanol (25 mL). After additionalrefluxing for 30 min, the mixture was cooled to room temperatureand the precipitate was filtered and washed with coldethanol. The obtained potassium 2,4-dioxothiazolidin-3-ide (2)(5 mmol) was refluxed with alkyl halides (5.5 mmol) in DMF(15 mL) for 3-4 h. After cooling to room temperature and additionof water (50 mL), the crude product was extracted 3 times withethyl acetate, washed with brine, and purified by flash chromatography(cyclohexane/ethyl acetate).

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5748 - 5755.

17
[ 2295-31-0 ]
[ 90176-80-0 ]
5-(4-fluoro-2-trifluoromethylbenzylidene)thiazolidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With piperidine; acetic acid; In toluene; at 80℃;Dean-Stark;	Thiazolidine-2,4-dione 1g (0.008538 mol), 4-Fluoro-2-trifluoromethyl-benzaldehyde 1.640 g, Piperidine 0.422ml, acetic acid 0.182ml and toluene 20ml were added to the dean-stark apparatus at 80 C, After reacting for 12 hours or longer, it was recrystallized to obtain pure 5- (4-Fluoro-2-trifluoromethyl-benzylidene) -thiazolidine-2,4-dione. Yield: 78%.

References: [1]Patent: KR2016/126772,2016,A .Location in patent: Paragraph 0339-0344.

18
[ 2295-31-0 ]
[ 63060-94-6 ]
[ 123-11-5 ]
[ 109-77-3 ]
C₂₅H₂₆N₄O₅S [ No CAS ]