Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate

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Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate Basic information
Product Name:Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate
Synonyms:Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate 97%;Ethyl imidazo[2,1-b]thiazole-6-carboxylate;IMIDAZO[2,1-B]THIAZOLE-6-CARBOXYLIC ACID ETHYL ESTER;ETHYL IMIDAZO[1,2-A]THIAZOLE-6-CARBOXYLATE;6-(Ethoxycarbonyl)imidazo[2,1-b][1,3]thiazole;Ethylimidazo[2,1-b][1,3]thiazole-6-carboxylate97%;SKL392;Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate
CAS:64951-04-8
MF:C8H8N2O2S
MW:196.23
EINECS:
Product Categories:
Mol File:64951-04-8.mol
Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate Structure
Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical Properties
Melting point 87 °C
CAS DataBase Reference64951-04-8
Safety Information
Hazard Note Harmful
HS Code 2934999090
MSDS Information
Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate Usage And Synthesis
Synthesis
2-Aminothiazole

96-50-4

Ethyl bromopyruvate

70-23-5

ETHYL IMIDAZO[2,1-B][1,3]THIAZOLE-6-CARBOXYLATE

64951-04-8

General procedure for the synthesis of ethylimidazo[2,1-b]thiazole-6-carboxylic acid from 2-aminothiazole (0.500 g, 5 mmol) and ethyl 3-bromopyruvate (90%, 1.625 g, 7.5 mmol): firstly, 2-amino thiazole was dissolved in tetrahydrofuran, followed by the addition of ethyl 3-bromopyruvate dropwise. The reaction mixture was stirred at room temperature for 8 hours before the precipitate was collected by filtration. The resulting filter cake was dissolved in hot ethanol and refluxed at 80°C for 8 hours. After completion of the reaction, the mixture was cooled and the solvent was removed by distillation. The residual solid was washed with cold water and filtered. After drying under vacuum, the intermediate (0.375 g) was obtained, which was dissolved in tetrahydrofuran. The yield of this step was 38.27%.

References[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 18, p. 3914 - 3929
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2764 - 2778
[3] Patent: CN105985356, 2016, A. Location in patent: Paragraph 0117; 0118
[4] Farmaco, Edizione Scientifica, 1977, vol. 32, # 10, p. 735 - 746
[5] Patent: US2010/249071, 2010, A1. Location in patent: Page/Page column 45
Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate Preparation Products And Raw materials
Raw materials2-Aminothiazole-->Ethyl bromopyruvate
Preparation ProductsImidazo[2,1-b][1,3]thiazole-6-carboxylic acid-->Imidazo[2,1-b]thiazole-6-carbaldehyde
Tag:Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate(64951-04-8) Related Product Information
Imidazo[2,1-b]thiazole-6-carbaldehyde 4-Ethoxycarbonylimidazole-2-thiol (2-Mercapto-1-methyl-1H-imidazol-5-yl)methanol Imidazo[2,1-b]thiazol-6-ylmethanol 3-Methylimidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester Ethyl imidazo[2,1-b][1,3]thiazole-6-carboxylate Imidazo[2,1-b][1,3]thiazole-6-carboxylic acid