Ethyl 2-methylthiazole-5-carboxylate

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CAS:79836-78-5
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Ethyl 2-methylthiazole-5-carboxylate Basic information
Product Name:Ethyl 2-methylthiazole-5-carboxylate
Synonyms:5-(Ethoxycarbonyl)-2-methyl-1,3-thiazole;ETHYL 2-METHYL-5-THIAZOLECARBOXYLATE;ETHYL 2-METHYL-THIAZOLE-5-CARBOXYLATE;2-METHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER;ETHYL2-METHYL-1,3-THIAZOLE-5-CARBOXYLATE;2-methyl-5-(carbethoxy)thiazole;5-Thiazolecarboxylicacid, 2-Methyl-, ethyl ester
CAS:79836-78-5
MF:C7H9NO2S
MW:171.22
EINECS:
Product Categories:Building Blocks;Thiazole series;Esters;Thiazoles, Isothiazoles &Benzothiazoles;Thiazole;Thiazoles, Isothiazoles & Benzothiazoles
Mol File:79836-78-5.mol
Ethyl 2-methylthiazole-5-carboxylate Structure
Ethyl 2-methylthiazole-5-carboxylate Chemical Properties
Boiling point 117-120 °C
density 1.198±0.06 g/cm3(Predicted)
storage temp. 2-8°C
form solid
pka1.61±0.10(Predicted)
AppearanceColorless to yellow Liquid
InChIKeyORCQTMZHDQSNOJ-UHFFFAOYSA-N
Safety Information
HS Code 2934100090
MSDS Information
Ethyl 2-methylthiazole-5-carboxylate Usage And Synthesis
Synthesis Reference(s)Journal of the American Chemical Society, 104, p. 4461, 1982 DOI: 10.1021/ja00380a022
Synthesis
Thioacetamide

62-55-5

2-Chloro-3-oxopropionic acid ethyl ester

33142-21-1

Ethyl 2-methylthiazole-5-carboxylate

79836-78-5

To a stirred solution of ethyl 2-chloro-3-oxopropanoate (5.0 g, 33 mmol) in benzene (50 mL) under argon protection was added thioacetamide (2.5 g, 33 mmol) and the mixture was heated to reflux. After 4 h, the reaction mixture was cooled to room temperature, diluted with water (50 mL) and neutralized with saturated sodium bicarbonate solution to pH 7. Subsequently, the reaction mixture was extracted with ethyl acetate and the organic phases were combined and washed sequentially with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification by silica gel column chromatography (eluent: heptane/ethyl acetate, 0 to 50% gradient) afforded ethyl 2-methylthiazole-5-carboxylate (2.68 g, 47% yield) as a yellow liquid. Mass spectrometry (MS) analysis showed: m/e = 172.0 [M + H]+.

References[1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4461 - 4465
[2] Patent: WO2010/127974, 2010, A1. Location in patent: Page/Page column 43
[3] Patent: WO2018/53157, 2018, A1. Location in patent: Page/Page column 108; 109
[4] Patent: WO2018/160878, 2018, A1. Location in patent: Page/Page column 278-279
[5] Journal of Chemical Research, 2011, vol. 35, # 5, p. 313 - 316
Ethyl 2-methylthiazole-5-carboxylate Preparation Products And Raw materials
Raw materialsThioacetamide-->2-Chloro-3-oxopropionic acid ethyl ester
Preparation Products(2-METHYL-1,3-THIAZOL-5-YL)METHYLAMINE
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