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ChemicalBook--->CAS DataBase List--->57626-37-6

57626-37-6

57626-37-6 Structure

57626-37-6 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

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

2-Aminothiazole

96-50-4

Ethyl 2-chloroacetoacetate

609-15-4

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

57626-37-6

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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