Identification | Back Directory | [Name]
ETHYL 3-METHYL-IMIDAZO[2,1-B]THIAZOLE 4-CARBOXYLATE | [CAS]
57626-37-6 | [Synonyms]
6-Methylimidazo[2,1-b][1,3]thiazole-5-carboxylate ETHYL 3-METHYL-IMIDAZO[2,1-B]THIAZOLE 4-CARBOXYLATE Ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate 6-methyl-5-imidazo[2,1-b]thiazolecarboxylic acid ethyl ester Imidazo[2,1-b]thiazole-5-carboxylic acid, 6-methyl-, ethyl ester | [Molecular Formula]
C9H10N2O2S | [MDL Number]
MFCD01060560 | [MOL File]
57626-37-6.mol | [Molecular Weight]
210.25 |
Chemical Properties | Back Directory | [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 |
Hazard Information | Back Directory | [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 |
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