Ethyl 2-chloro-6-benzothiazolecarboxylate Chemical Properties

Melting point:

90-92°

Boiling point:

340.5±15.0 °C(Predicted)

Density 

1.400

storage temp. 

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

pka

-1.37±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C10H8ClNO2S/c1-2-14-9(13)6-3-4-7-8(5-6)15-10(11)12-7/h3-5H,2H2,1H3

InChIKey

XISSCVMIXDMKLH-UHFFFAOYSA-N

SMILES

S1C2=CC(C(OCC)=O)=CC=C2N=C1Cl

Safety Information

HazardClass 

IRRITANT

HS Code 

2934208090

Ethyl 2-chloro-6-benzothiazolecarboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 2-chlorobenzo[d]thiazole-6-carboxylate from ethyl 2-aminobenzo[d]thiazole-6-carboxylate: In a 500 mL single-necked flask, copper chloride (6.0 g, 44.6 mmol), tert-butyl nitrite (7.1 mL, 59.4 mmol), and acetonitrile (200 mL) were added and the mixture was cooled to 0 °C. Subsequently, ethyl 2-aminobenzo[d]thiazole-6-carboxylate (6.6 g, 29.7 mmol) was added in batches over 30 min. The reaction mixture was gradually warmed to room temperature and stirred overnight. After completion of the reaction, the filtrate was filtered through silica gel and the filtrate was added dropwise to 1 M HCl (60 mL) and stirred for 10 min to form a partition. The aqueous layer was extracted with ethyl acetate (100 mL), the organic layers were combined, washed with saturated brine and dried over anhydrous Na2SO4. After filtration again, it was rotary evaporated to dryness and purified by column chromatography (petroleum ether:ethyl acetate = 25:1) to afford 6.2 g of a pale yellow solid, ethyl 2-chlorobenzo[d]thiazole-6-carboxylate, in 86% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.54 (d, J = 0.8 Hz, 1H), 8.20 (dd, J = 1.6 Hz, 8.4 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H), 4.45 (q, J = 7.2 Hz, 2H), 1.45 (t, J = 7.2 Hz, 3H).

References

[1] Patent: EP3401315, 2018, A1. Location in patent: Paragraph 0062; 0064
[2] Farmaco, 1994, vol. 49, # 3, p. 153 - 166

Ethyl 2-chloro-6-benzothiazolecarboxylate(78485-37-7)Related Product Information

• Ethanol
• Ethyl acrylate
• Ethyl cellulose
• Ethyl acetate
• Ethyl formate
• Urethane
• 2-Chlorobenzothiazole
• Tris(trimethylsilyl)phosphate
• 2,2'-Dithiobis(benzothiazole)
• Epichlorohydrin
• Ethylparaben
• 2-Mercaptobenzothiazole
• Triethyl orthoformate
• Benzothiazole
• Ethyl chloroformate
• Difluorochloromethane
• Diethyl ether
• Chloroacetic acid