Ethyl 4-methyl-5-thiazoleactate

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CAS:20582-55-2
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Products Intro: Product Name:Ethyl 4-methyl-5-thiazoleactate
CAS:20582-55-2

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Ethyl 4-methyl-5-thiazoleactate Basic information
Product Name:Ethyl 4-methyl-5-thiazoleactate
Synonyms:ETHYL 4-METHYLTHIAZOLE-5-CARBOXYLATE;ETHYL 4-METHYL-5-THIAZOLEACTATE;ETHYL 4-METHYL-5-THIAZOLYL FORMATE;5-THIAZOLECARBOXYLIC ACID, 4-METHYL-, ETHYL ESTER;Ethyl-4-methyl-5-thizaolecarboxylate;4-Methyl-5-Thiazolecarboxylic Acid Ethyl Ester;ETHYL 4-METHYL-5-THIAZOLECARBOXYLATE;ethyl 4-methyl-1,3-thiazole-5-carboxylate
CAS:20582-55-2
MF:C7H9NO2S
MW:171.22
EINECS:
Product Categories:Febuxostat
Mol File:20582-55-2.mol
Ethyl 4-methyl-5-thiazoleactate Structure
Ethyl 4-methyl-5-thiazoleactate Chemical Properties
Melting point 28°C(lit.)
Boiling point 233°C(lit.)
density 1.198±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form powder to lump
pka1.57±0.10(Predicted)
color White to Almost white
LogP1.410 (est)
CAS DataBase Reference20582-55-2(CAS DataBase Reference)
Safety Information
HazardClass IRRITANT
HS Code 2934208090
MSDS Information
Ethyl 4-methyl-5-thiazoleactate Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
Synthesis
Ethyl 2-amino-4-methylthiazole-5-carboxylate

7210-76-6

Ethyl 4-methyl-5-thiazoleactate

20582-55-2

General procedure for the synthesis of ethyl 4-methylthiazole-5-carboxylate from ethyl 2-amino-4-methylthiazole-5-carboxylate: compound 3a (4.0 g, 21.5 mmol) was dissolved in 106 mL of 30% hypophosphite (H3PO2) solution. The reaction system was cooled to -5°C, after which sodium nitrite (NaNO2, 3.0 g, 2.0 eq.) was dissolved in 12 mL of water and slowly added dropwise to the reaction solution. After the dropwise addition, the reaction mixture was transferred to 0°C and kept for 1 hour, then stirring was continued for 2 hours at room temperature. Subsequently, pre-cooled sodium hydroxide solution (17 g NaOH dissolved in 200 mL of water) was added slowly dropwise. The reaction mixture was adjusted to neutral with sodium bicarbonate (NaHCO3) solution and then extracted with ether (Et2O, 50 mL x 3). The organic phases were combined and purified by column chromatography (eluent ratio: petroleum ether:ethyl acetate = 50:1, v/v) to give the yellow semi-solid product 3b (2.1 g, 56% yield).

References[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6231 - 6235
[2] Patent: CN101921268, 2016, B. Location in patent: Paragraph 0128; 0131; 0136-0139
[3] Tetrahedron, 2013, vol. 69, # 22, p. 4436 - 4444
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