6-Benzothiazolecarboxylicacid,methylester(9CI) Chemical Properties

Melting point:

106-107 °C

Boiling point:

309.9±15.0 °C(Predicted)

Density 

1.340±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-0.35±0.10(Predicted)

Appearance

White to light yellow Solid

6-Benzothiazolecarboxylicacid,methylester(9CI) Usage And Synthesis

Synthesis

1. 1,3-Benzothiazole-6-carboxylic acid (5.0 g, 27.93 mmol) was dissolved in a solvent mixture of dichloromethane (96 mL) and methanol (32 mL) and the solution was cooled to 0°C. 2. A hexane solution of trimethylsilylated diazomethane (28 mL, 2.0 M) was slowly added dropwise with stirring. 3. After the dropwise addition is complete, the reaction mixture is gradually warmed to room temperature and stirring is continued overnight. 4. Upon completion of the reaction, acetic acid (2 mL) was carefully added to quench the reaction and stirring was continued for 30 minutes. 5. The reaction solution was concentrated, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. 6. Separate the organic layer, dry with anhydrous sodium sulfate, filter and concentrate under reduced pressure. 7. The crude product was purified by silica gel column chromatography using 15% ethyl acetate/hexane as eluent to afford methyl 6-benzothiazolecarboxylate (4.44 g, 82% yield) as a white solid. 8. The structure of the product was determined by 1H2O2 chromatography. 8. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 9.15 (s, 1H), 8.68 (m, 1H), 8.16 (m, 2H), 3.97 (s, 3H).

References

[1] Patent: US2006/40927, 2006, A1. Location in patent: Page/Page column 38

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