ChemicalBook CAS DataBase List (2-BENZOTHIAZOLYLTHIO)ACETIC ACID

(2-BENZOTHIAZOLYLTHIO)ACETIC ACID synthesis

8synthesis methods

Product Name:(2-BENZOTHIAZOLYLTHIO)ACETIC ACID
CAS Number:6295-57-4
Molecular formula:C9H7NO2S2
Molecular Weight:225.29

79-08-3 Synthesis

79-08-3
310 suppliers
$9.00/1g

149-30-4
644 suppliers
$5.00/25g

6295-57-4
147 suppliers
$7.00/5g

Yield:6295-57-4 89%

Reaction Conditions:

with potassium hydroxide in ethanol at 20; for 3 h;

Steps:

2-(Benzo[d]thiazol-2-ylthio)acetic acid (48).

Bromoacetic acid (1.390g, 10mmol) in ethanol (15mL) was dropwise added to a solution of 44 (836mg, 5mmol) in ethanol (15mL). Then, 2M KOH (30mL) was added and the reaction mixture was stirred for 3hat room temperature. After TLC control (EtOAc/Hexane 5:5), the reaction mixture was diluted with water (60mL) and acidified with 6N HCl, affording a solid product 48 that was isolated by filtration (1g, 4.44mmol). Yield: 89%. ¹H NMR (500MHz, DMSO-d₆, δ): 4.21 (s, 2H), 7.32-7.34 (m, 1H), 7.42-7.45 (m, 1H), 7.79-7.81 (m, 1H), 7.97-7.99 (m, 1H), 13.02 (bs, 1H, exchanges with D₂O).

References:

Savino, Salvatore;Toscano, Annamaria;Purgatorio, Rosa;Profilo, Emanuela;Laghezza, Antonio;Tortorella, Paolo;Angelelli, Mariacristina;Cellamarea, Saverio;Scala, Rosa;Tricarico, Domenico;Thomas Marobbio, Carlo Marya;Perna, Filippo;Vitale, Paola;Agamennone, Mariangela;Dimiccoli, Vincenzo;Tolomeo, Anna;Scilimati, Antonio [European Journal of Medicinal Chemistry,2018,vol. 158,p. 184 - 200]

24044-88-0 Synthesis