4-Hydroxy-2-methylthiazole-5-carboxylicacidethylester Chemical Properties

Melting point:

104°

Boiling point:

270.7±20.0 °C(Predicted)

Density 

1.325±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

8.56±0.20(Predicted)

Safety Information

HS Code 

2934100090

4-Hydroxy-2-methylthiazole-5-carboxylicacidethylester Usage And Synthesis

Synthesis

5.2 Synthesis of 2-methyl-5-ethoxycarbonyl-4-hydroxythiazole: Diethyl 2-bromomalonate (168 g, 0.7 mol) was slowly added to a 400 mL solution of toluene containing thioacetamide (52.5 g, 0.7 mol). The reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad. Subsequently, the toluene was evaporated under reduced pressure to give a viscous oily crude product. This crude product was mixed with 500 mL of water and stirred until solids precipitated. The solid product was collected by filtration, washed sequentially with water (3 x 300 mL) and petroleum ether, and finally dried under high vacuum to afford 55 g of methyl 4-hydroxy-2-methylthiazole-5-carboxylate (yield: 42%; LC retention time: 1.24 min; MS: [M+H]+ = 188).

References

[1] Patent: WO2005/97766, 2005, A1. Location in patent: Page/Page column 28-29
[2] Patent: WO2010/59838, 2010, A2. Location in patent: Page/Page column 124
[3] Patent: WO2014/82737, 2014, A1. Location in patent: Page/Page column 43
[4] Patent: WO2008/152390, 2008, A1. Location in patent: Page/Page column 33; 46-47
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 970 - 986

4-Hydroxy-2-methylthiazole-5-carboxylicacidethylester(20737-48-8)Related Product Information

• Thiazole-5-carboxylic acid
• 2-Methylthiazole
• ETHYL 2-(2-CHLOROPHENYL)-4-HYDROXY-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 4-HYDROXY-2-(4-METHYLPHENYL)-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 4-HYDROXY-2-PHENYL-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 2-(3,4-DIMETHOXYPHENYL)-4-HYDROXY-1,3-THIAZOLE-5-CARBOXYLATE
• 4-Hydroxy-2-methylthiazole-5-carboxylicacidethylester
• ETHYL 2-(2,4-DICHLOROPHENYL)-4-HYDROXYTHIAZOLE-5-CARBOXYLATE
• ETHYL 4-HYDROXY-2-(4-METHOXYPHENYL)-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 4-HYDROXY-2-(2-THIENYL)-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 4-HYDROXY-2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 2-(4-CHLOROPHENYL)-4-HYDROXY-1,3-THIAZOLE-5-CARBOXYLATE
• ETHYL 4-HYDROXY-2-[3-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE-5-CARBOXYLATE