ETHOXY-IMINO-ACETIC ACID ETHYL ESTER Chemical Properties

Boiling point:

151℃

Density 

1.08

refractive index 

n20/D1.426

Flash point:

45℃

storage temp. 

-20°C

pka

3.21±0.70(Predicted)

form 

liquid

color 

Clear, light yellow

InChI

InChI=1S/C6H11NO3/c1-3-9-5(7)6(8)10-4-2/h7H,3-4H2,1-2H3

InChIKey

DSHWMBCJDOGPTB-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(OCC)=N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2922500090

ETHOXY-IMINO-ACETIC ACID ETHYL ESTER Usage And Synthesis

Synthesis

Ethyl cyanoacetate (40 g, 404 mmol) was dissolved in dichloromethane (200 mL) and cooled to 0°C under nitrogen protection. An ethanol solution of 45 wt.% hydrochloric acid (27.3 mL, 404 mmol) was added slowly and dropwise over 15 min with stirring. The reaction mixture was stirred continuously at 0 °C for 3 h, followed by standing overnight at -5 °C to -3 °C. The following day, dichloromethane (250 mL) was added to the reaction mixture and kept at 0 °C. A solution of triethylamine (113 mL, 807 mmol) in dichloromethane (50 mL) was added dropwise over 30 minutes. After the dropwise addition, the mixture was continued to be stirred at 0°C for 30 minutes. Subsequently, water (100 mL) was added and stirred for 5 minutes. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Diethyl ether (50 mL) was added to the residue and the solid was removed by filtration. The filtrate was dried to give ethyl 2-ethoxy-2-iminoacetate as a light yellow liquid (31.0 g, 214 mmol, 52.9% yield). NMR hydrogen spectrum (400 MHz, CDCl3) δ 8.78 (s, 1H), 4.36-4.28 (m, 4H), 1.40-1.35 (m, 6H).

References

[1] Synthesis, 1997, # 3, p. 301 - 304
[2] Patent: WO2018/154520, 2018, A1. Location in patent: Page/Page column 92
[3] Helvetica Chimica Acta, 1989, vol. 72, p. 825 - 837
[4] Helvetica Chimica Acta, 1989, vol. 72, p. 825 - 837
[5] Patent: WO2009/155121, 2009, A2. Location in patent: Page/Page column 106

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