Synthesis of 2‐oxo‐3‐benzothiazolineacetyl chloride (7), 5‐chloro‐2‐oxo‐3‐benzothiazolineacetyl chloride (8) and derivatives

Abstract

The reaction of 2‐oxo‐3‐benzothiazolineacetic acid (5) and the 5‐chloro analogue 6 with thionyl chloride afforded the titled compounds 7 and 8. The reaction of 7 or 8 with substituted hydrazines, amines or substituted anilines, alcohols and mercaptans furnished the hydrazides 9–14, acetamides and acetanilides 16–21, esters 26–30 and thiolesters 31–37, respectively. Alternate routes for the synthesis of hydrazide 15, acetamides and acetanilides 22–25 and thiolesters 35–36 are described. The reaction of 2‐oxo‐3(2H)‐benzothi‐azolineacetonitrile with thioacetic acid under acidic conditions afforded 2‐oxo‐3‐benzothiazolineethanethio‐amide (38).

Synthesis, DFT Calculations, and Molecular Docking Study of Acetohydrazide‐Based Sulfonamide Derivatives as Paraoxonase 1 Inhibitors

“…The mechanism of binding for the relatively active compounds on paraoxonase 1 was assessed through molecular docking. The missing residues in the PDB structure retrieved were generated by using homology modeling, which is widely used for this purpose [44,45] . The docking process was validated by performing the molecular docking of the ligand bound in the utilized structure (3SRG), 2‐hydroxyquinoline.…”

“…The missing residues in the PDB structure retrieved were generated by using homology modeling, which is widely used for this purpose. [44,45] The docking process was validated by performing the molecular docking of the ligand bound in the utilized structure (3SRG), 2-hydroxyquinoline. The bound ligand had good interactions with paraoxonase 1.…”

Synthesis, Structure and Antifungal Activity of New 3-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol-2(3H)-ones

“…5-Chloro-2(3H)-benzothiazolone ( 1 b , R = Cl): yield 77.0%; m.p. 240–241 °C (239–240 °C, lit [ 23 ]). 1 H-NMR (CDCl 3 ) δ: 7.19 ~ 7.50 (m, 3H, ArH), 9.77 (s, NH, 1H).…”

“…Ethyl 2-(5-chloro-2-oxobenzothiazolin-3-yl)acetate ( 2b ): 24.3 g, yield 94.3%, white solid, m.p. 113–115 °C (115–116 °C, lit [ 23 ]).…”

Synthesis and Antinociceptive Activity of (5-Chloro-2-benzothiazolinon-3-yl)acetamide Derivatives

“…Synthesis of the compounds was started by obtaining 5-chloro-2-benzothiazolinone V from 2,5-dichloronitrobenzene. Syntheses of (5-chloro-2-benzothiazolinon-3-yl)-acetic acid VI and (5-chloro-2-benzothiazolinon-3-yl)-acetyl chloride VII were previously reported by other authors [15] . According to the method reported in the literature, 5-chloro-2(3H)-benzothiazolone was reacted with chloroacetic acid to form VI, and the acid thus obtained was reacted with thionyl chloride to obtain VII.…”