N-CARBOXYETHYLRHODANINE Chemical Properties

Melting point:

158-160°C

Boiling point:

385.9±44.0 °C(Predicted)

Density 

1.61±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.36±0.10(Predicted)

color 

Light yellow to Brown

CAS DataBase Reference

7025-19-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RTECS 

XJ6094060

HS Code 

2934.10.9000

HazardClass 

IRRITANT

N-CARBOXYETHYLRHODANINE Usage And Synthesis

Synthesis

Synthesis of 3-(4-oxo-2-thioxothiazolidin-3-yl)propionic acid (33): β-alanine 32 (3.4 g, 38.1 mmol) was dissolved in 17 mL of 22% potassium hydroxide solution, and the temperature of the reaction was controlled not to exceed 25 °C. Carbon disulfide (2.5 mL, 42 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature. Subsequently, batchwise addition of bromoacetic acid (5.3 g, 38.1 mmol) was made over about 20 minutes, and the whole process was completed in about 3 hours. After addition, stirring was continued at room temperature for 3 hours, during which precipitation was observed. The pH of the reaction mixture was adjusted with concentrated hydrochloric acid to 3-4. After addition of sulfuric acid, the solution was stirred at room temperature overnight. The precipitate was collected by filtration and washed with water to give pure target compound 33 (3.52 g, 45% yield) as a yellow solid. Melting point 155-156 °C. 1H NMR (400 MHz, MeOD-d4) δ (ppm): 5.00 (brs, 1H), 4.22 (t, J = 7.5 Hz, 2H), 4.11 (s, 1H), 2.64 (t, J = 7.6 Hz, 2H). 13C NMR (100 MHz, MeOD-d4) δ (ppm): 202.58, 174.37, 172.87, 39.64, 35.08, 30.28. mass spectrum (ESI) m/z: 204.1 [M-H]+. Elemental analysis (C6H7NO3S2) Calculated values: C, 35.11; H, 3.44; N, 6.82. Measured values: C, 35.10; H, 3.48; N, 6.88.

References

[1] ChemMedChem, 2014, vol. 9, # 11, p. 2538 - 2547
[2] Patent: WO2011/39735, 2011, A2. Location in patent: Page/Page column 149-150
[3] ChemMedChem, 2014, vol. 9, # 11, p. 2538 - 2547

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