ETHYL 3-AMINO-3-THIOXOPROPANOATE Chemical Properties

Melting point:

78-79℃

Boiling point:

233℃

Density 

1.194

Flash point:

95℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

12.71±0.29(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C5H9NO2S/c1-2-8-5(7)3-4(6)9/h2-3H2,1H3,(H2,6,9)

InChIKey

IBHOWDPRDYMIMO-UHFFFAOYSA-N

SMILES

C(OCC)(=O)CC(N)=S

ETHYL 3-AMINO-3-THIOXOPROPANOATE Usage And Synthesis

Synthesis

Step A: Ethyl cyanoacetate (4.7 mL, 44.3 mmol) was dissolved in a pyridine/triethylamine solvent mixture (500 mL, 1:1 v/v) under nitrogen protection. Hydrogen sulfide gas (H2S) was slowly passed into the solution until saturation. The reaction mixture was heated to 60 °C and stirred for 18 hours. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was separated by extraction with ethyl acetate (EtOAc) and dilute hydrochloric acid aqueous solution. The organic layer was dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. Removal of residual solid impurities by filtration afforded ethyl 3-amino-3-thiopropionate (6.25 g, 96% yield) as an orange oil. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 8.92 (1H, broad single peak), 7.75 (1H, broad single peak), 4.21 (2H, quadruple peak, J = 7 Hz), 3.82 (2H, single peak), 1.29 (3H, triple peak, J = 7 Hz).

References

[1] Patent: WO2013/101974, 2013, A1. Location in patent: Paragraph 00704; 00705
[2] Patent: US9617268, 2017, B2. Location in patent: Page/Page column 347; 348
[3] Synlett, 2009, # 14, p. 2338 - 2340
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 325 - 326
[5] Helvetica Chimica Acta, 1948, vol. 31, p. 1342,1348

ETHYL 3-AMINO-3-THIOXOPROPANOATE(13621-50-6)Related Product Information

• isopropyl 3-amino-3-thioxopropanoate
• ETHYL 3-ANILINO-3-THIOXOPROPANOATE
• CBI-BB ZERO/005131
• ETHYL 2-[(METHYLAMINO)CARBONOTHIOYL]-3-OXOBUTANOATE
• 5-AMINO-2-PHENYL-3-THIOXO-2,3-DIHYDRO-ISOTHIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• 6-METHYL-2-OXO-4-THIOXO-1,2,3,4-TETRAHYDRO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER
• SALOR-INT L307580-1EA
• DIETHYL (ANILINOCARBONOTHIOYL)MALONATE
• ETHYL 3-AMINO-3-THIOXOPROPANOATE