ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate

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ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate Basic information
Product Name:ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate
Synonyms:ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate;Butanoic acid, 2-[(dimethylamino)methylene]-3-oxo-, ethyl ester, (2E)-
CAS:203186-58-7
MF:C9H15NO3
MW:185.22
EINECS:
Product Categories:
Mol File:203186-58-7.mol
ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate Structure
ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate Chemical Properties
Boiling point 246.3±30.0 °C(Predicted)
density 1.038±0.06 g/cm3(Predicted)
pka3.52±0.70(Predicted)
Safety Information
MSDS Information
ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate Usage And Synthesis
Uses(E)-Ethyl 2-((dimethylamino)methylene)-3-oxobutanoate, can be used in the synthesis of N-substituted-[1,2,4]triazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines having antibacterial activity.
Synthesis
Ethyl acetoacetate

141-97-9

N,N-Dimethylformamide dimethyl acetal

4637-24-5

ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate

203186-58-7

To a solution of ethyl acetoacetate (2.6 g, 20 mmol) in ethanol (10 mL) was added N,N-dimethylformamide dimethyl acetal (2.5 g, 21 mmol). The reaction mixture was stirred at 60°C for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to afford the crude product ethyl (E)-2-((dimethylamino)methylene)-3-oxobutanoate (3.6 g, 97% yield), which could be used in the subsequent reaction without further purification.

References[1] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1038 - 1043
[2] Patent: WO2017/151786, 2017, A1. Location in patent: Paragraph 00230
ethyl(E)-2-((dimethylamino)methylene)-3-oxobutanoate Preparation Products And Raw materials
Raw materialsEthyl acetoacetate-->N,N-Dimethylformamide dimethyl acetal
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