Ethyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical Properties

Melting point:

241-243°C

Boiling point:

386.8±34.0 °C(Predicted)

Density 

1.364±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.79±0.10(Predicted)

form 

Solid

color 

White to Orange to Green

InChI

InChI=1S/C10H10N2O2S/c1-2-14-9(13)6-3-4-7-8(5-6)15-10(11)12-7/h3-5H,2H2,1H3,(H2,11,12)

InChIKey

VYJSGJXWKSDUSG-UHFFFAOYSA-N

SMILES

S1C2=CC(C(OCC)=O)=CC=C2N=C1N

CAS DataBase Reference

50850-93-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2934208090

Ethyl 2-amino-1,3-benzothiazole-6-carboxylate Usage And Synthesis

Chemical Properties

yellow crystal

Uses

Ethyl 2-amino-benzothiazole-6-carboxylate (cas# 50850-93-6) is a compound useful in organic synthesis.

Synthesis

Ethyl 4-aminobenzoate (4.9 g, 30.0 mmol) was dissolved with potassium thiocyanate (11.6 g, 120.0 mmol) in acetic acid (180 mL), followed by the slow dropwise addition of acetic acid solution (20 mL) containing bromine (1.5 mL, 30.0 mmol). The reaction was carried out at 19 °C and the titration process was controlled to be completed within 20 min. After the dropwise addition, the reaction system was gradually warmed up to room temperature and the reaction was continued with stirring overnight. Upon completion of the reaction, the reaction solution was slowly poured into water (100 mL) and stirred for 10 minutes. Subsequently, ammonium hydroxide solution was added dropwise to the mixture and the pH was adjusted to about 8. The reaction mixture was filtered and the resulting filter cake was washed sequentially with water. Finally, the product was dried under vacuum to give 6.7 g of yellow solid, ethyl 2-aminobenzo[d]thiazole-6-carboxylate in 100% yield. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO): δ 8.28 (d, J = 1.6 Hz, 1H), 7.88 (s, 2H), 7.82 (dd, J = 1.6 Hz, 8.4 Hz, 1H), 7.37 (d, J = 8.4 Hz, 1H), 4.29 (q, J = 7.2 Hz, 2H), 1.32 (t, J = 7.2 Hz, 3H).

References

[1] Patent: EP3401315, 2018, A1. Location in patent: Paragraph 0062; 0063
[2] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[3] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 702 - 712
[4] Medicinal Chemistry, 2017, vol. 13, # 4, p. 345 - 358
[5] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40

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