ETHYL 2-CHLOROTHIAZOLE-5-CARBOXYLATE Chemical Properties

Boiling point:

283.9±32.0 °C(Predicted)

Density 

1.383±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform; Dichloromethane; DMSO; Ethyl Acetate

pka

-0.98±0.10(Predicted)

form 

Oil

color 

Colorless

CAS DataBase Reference

81449-93-6(CAS DataBase Reference)

Safety Information

HS Code 

2934100090

ETHYL 2-CHLOROTHIAZOLE-5-CARBOXYLATE Usage And Synthesis

Uses

Ethyl 2-chlorothiazole-5-carboxylate is an intermediate in synthesizing 2-Chloro-5-thiazolecarboxylic Acid (C411465). It was studied as one of the metabolites of thiamethoxam, clothianidin, and dinotefuran in mice.

Synthesis

The general procedure for the synthesis of ethyl 2-chloro-1,3-thiazole-5-carboxylate from ethyl 2-aminothiazole-5-carboxylate was as follows: ethyl 2-aminothiazole-5-carboxylate (1.0 g, 6.35 mmol) was dissolved in a solvent mixture of acetonitrile (10 mL) and tetrahydrofuran (10 mL) at 23 °C. The solution was then slowly added to a mixture of acetonitrile (10 mL) and tetrahydrofuran (10 mL) containing butyl nitrite (1.3 mL, 9.52 mmol) and cuprous chloride (1.0 g, 7.6 mmol). The reaction mixture was to be heated at 65°C until thin layer chromatography (TLC) analysis (unfolding agent was 40% ethyl acetate-hexane) showed complete consumption of the raw materials. After completion of the reaction, the mixture was cooled to room temperature and extracted by partitioning between water and ethyl acetate. The organic layer was collected, concentrated under reduced pressure and finally purified by fast silica gel column chromatography with 20% ethyl acetate-hexane as eluent to afford the target product ethyl 2-chloro-1,3-thiazole-5-carboxylate (0.49 g, 40% yield).

References

[1] Patent: EP2615092, 2013, A1. Location in patent: Paragraph 0095; 0097
[2] Helvetica Chimica Acta, 1954, vol. 37, p. 2057,2064
[3] Helvetica Chimica Acta, 1944, vol. 27, p. 1432,1433
[4] Patent: WO2004/80996, 2004, A1. Location in patent: Page 26-27; 47

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