Benzothiazole, 2-chloro-4-methoxy- (6CI,7CI,8CI,9CI) Chemical Properties

Melting point:

66 °C

Boiling point:

293.5±13.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.08±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C8H6ClNOS/c1-11-5-3-2-4-6-7(5)10-8(9)12-6/h2-4H,1H3

InChIKey

MCCTXJVKIFYBJV-UHFFFAOYSA-N

SMILES

S1C2=CC=CC(OC)=C2N=C1Cl

Safety Information

HS Code 

29342000

Benzothiazole, 2-chloro-4-methoxy- (6CI,7CI,8CI,9CI) Usage And Synthesis

Chemical Properties

Pale yellow liquid

Synthesis

The general procedure for the synthesis of 2-chloro-4-methoxybenzo[d]thiazole using 2-amino-4-methoxybenzothiazole as starting material was as follows: copper(II) chloride (3.36 g, 25.0 mmol), acetonitrile (71 mL), and isoamyl nitrite (2.2 mL, 16.6 mmol) were added to a 500 mL three-neck flask equipped with a condenser under nitrogen protection. The suspension was placed in a 65 °C oil bath and stirred for 10 min, followed by the slow addition of a solution of 2-amino-4-methoxybenzothiazole (2.00 g, 11.1 mmol) in acetonitrile (42 mL). The reaction mixture was stirred continuously in an oil bath at 65 °C for 2 h and subsequently cooled to 20 °C. Water (150 mL) and 1N hydrochloric acid (100 mL) were added to the reaction mixture, followed by extraction with ethyl acetate (3 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography (5% to 15% gradient with ethyl acetate in hexane as eluent) to afford 2-chloro-4-methoxybenzo[d]thiazole (1.52 g, 69% yield) as a white solid.

References

[1] Patent: WO2016/197078, 2016, A1. Location in patent: Paragraph 626
[2] Gazzetta Chimica Italiana, 1964, vol. 94, p. 372 - 381

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