ETHYL 3-METHYL-IMIDAZO[2,1-B]THIAZOLE 4-CARBOXYLATE Chemical Properties

Melting point:

98 °C

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.81±0.40(Predicted)

Appearance

White to off-white Solid

ETHYL 3-METHYL-IMIDAZO[2,1-B]THIAZOLE 4-CARBOXYLATE Usage And Synthesis

Uses

Ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate

Synthesis

The reaction was carried out with 2-aminothiazole (3.00 g, 29.99 mmol) and ethyl 2-chloroacetoacetate (4.96 mL, 35.99 mmol) in 1,2-dimethoxyethane (30 mL) at 90 °C for 6 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate (80 mL), followed by washing the organic layer with water (3 x 30 mL). The organic layer was separated and dried with anhydrous sodium sulfate and concentrated in vacuum to obtain the crude product. The crude product was purified by column chromatography using 20% ethyl acetate/hexane as eluent to give ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate (2a) (5.20 g, 82% yield) as an off-white solid. The molecular weight of the product was confirmed to be 211 [M + H]+ by electrospray ionization mass spectrometry (ESIMS), followed by the next step of the reaction.

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1298 - 1307
[2] European Journal of Medicinal Chemistry, 1994, vol. 29, # 12, p. 981 - 983
[3] Patent: WO2010/90716, 2010, A1. Location in patent: Page/Page column 328
[4] Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 533 - 545
[5] Archiv der Pharmazie, 1976, vol. 309, # 12, p. 959 - 965

ETHYL 3-METHYL-IMIDAZO[2,1-B]THIAZOLE 4-CARBOXYLATE(57626-37-6)Related Product Information

• Ethyl 2-Methyl-Imidazo[2,1-B]Thiazole-3-Carboxylate
• ETHYL 6-(3-CHLOROPHENYL)IMIDAZO[2,1-B]THIAZOLE-5-CARBOXYLATE
• ETHYL 6-THIOPHENOIMIDAZOLE-2-METHOXYMETHYL-3-CARBOXYLATE
• ETHYL 6-(2-CYCLOPENTYLETHYL)IMIDAZO[2,1-B]THIAZOLE-5-CARBOXYLATE
• ETHYL 3-METHYL-IMIDAZO[2,1-B]THIAZOLE 4-CARBOXYLATE
• IMIDAZO[2,1-B]THIAZOLE-5-CARBOXYLIC ACID, 6-(1-METHYLETHYL)-, ETHYL ESTER