ChemicalBook CAS DataBase List 2(3H)-Benzothiazolone,6-acetyl-(9CI)

2(3H)-Benzothiazolone,6-acetyl-(9CI) synthesis

5synthesis methods

Product Name:2(3H)-Benzothiazolone,6-acetyl-(9CI)
CAS Number:133044-44-7
Molecular formula:C9H7NO2S
Molecular Weight:193.22

934-34-9 Synthesis

934-34-9
236 suppliers
$10.00/1g

75-36-5 Synthesis

75-36-5
579 suppliers
$17.92/100G

133044-44-7
65 suppliers
$25.60/1g

Yield: 90%

Reaction Conditions:

with aluminum (III) chloride;N,N-dimethyl-formamide at 90; for 8 h;

Steps:

4.1.15 6-acetyl-3H-benzothiazol-2-one (16)
DMF (9mL, 116.2mmol) is added dropwise to AlCl₃ (44,2g, 332mmol) in powder and the resulting mixture is stirred at room temperature for 20min. Benzothiazol-2-one 7 (5g, 33.2mmol) and acetyl chloride (2.8mL, 39.8mmol) are added and the resulting solution is stirred at 90°C for 8h. The reaction mixture is poured into ice-water and the resulting solid is filtered and washed with water. Recrystallization from ethanol yielded 16 as a beige powder (5.77g, 90%); C₉H₇NO₂S; MW=193.23g/mol; m.p. 189-191°C (ref); ¹H NMR (CDCl₃): δ 2.54 (s, 3H); 7.19 (d, 2H, J=8.5Hz); 7.89 (dd, 1H, J=1.75Hz, 8.5Hz); 8.24 (d, 1H, J=1.75Hz); 12.09 (s, 1H). MS (ESI⁺) m/z 194.1 [M+H]⁺.

References:

Pirat, Celine;Dacquet, Catherine;Leclerc, Veronique;Hennuyer, Nathalie;Beucher-Gaudin, Monique;Zanirato, Ghislaine;Géant, Anne;Staels, Bart;Ktorza, Alain;Farce, Amaury;Caignard, Daniel-Henri;Berthelot, Pascal;Lebegue, Nicolas [European Journal of Medicinal Chemistry,2017,vol. 137,p. 310 - 326]