3-METHYL-1,3-THIAZOLANE-2,4-DIONE Chemical Properties

Melting point:

40-43°C

Boiling point:

130-131 °C(Press: 14 Torr)

Density 

1.421±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.27±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C4H5NO2S/c1-5-3(6)2-8-4(5)7/h2H2,1H3

InChIKey

HMLWNNMYODLLJO-UHFFFAOYSA-N

SMILES

S1CC(=O)N(C)C1=O

Safety Information

HazardClass 

IRRITANT

HS Code 

2934999090

3-METHYL-1,3-THIAZOLANE-2,4-DIONE Usage And Synthesis

Uses

3-methyl-1,3-thiazolidine-2,4-dione can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

To a solution of 2,4-thiazolidinedione (1 equiv) in 5 mL of DMF was added potassium carbonate (1.1 equiv) and halogen (1.1 equiv). The suspension was stirred at 80 oC overnight. Solvent was evaporated and the residue was purified by flash column chromatography ( petroleum ether/EtOAc, 5:1) to afford the product 3. 3-Methylthiazolidine-2,4-dione (3a) Following the previous procedure, 2,4-thiazolidinedione (500 mg, 4.3 mmol) and iodomethane (0.3 mL, 4.7 mmol). 3a as white solid (460 mg, 82%).

References

[1] Journal of Chemical Research, 2005, # 8, p. 492 - 494
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3801 - 3807
[3] Organic Letters, 2015, vol. 17, # 6, p. 1361 - 1364
[4] Patent: WO2012/137181, 2012, A1. Location in patent: Page/Page column 136-137
[5] Patent: WO2017/176812, 2017, A1. Location in patent: Paragraph 0503

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