Water → 5-(4-(6-methoxyquinolin-2-yl)phenyl)-1,2,4-thiadiazol-3(2H)-one

https://huagongshe.com/reaction/2201449

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Oxalyl chloride	HCID 65578	—
Reactant	Azidotrimethylsilane	HCID 78378	—
Reactant	4-(6-Methoxyquinolin-2-yl)benzothioamide	HCID 87223412	—
Solvent	1,2-Dichloroethane	HCID 11	—
Solvent	Isopropanol	HCID 3776	—
Product	5-(4-(6-methoxyquinolin-2-yl)phenyl)-1,2,4-thiadiazol-3(2H)-one	HCID 66980084	78%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 4-(6-methoxyquinolin-2-yl)benzothioamide (500 mg, 1.07 mmol) in DCE (10 mL) was added oxalylchloride (0.3 mL, 3.9 mmol) dropwise at 0° C. The mixture was heated to 90° C. for 2 hours. TMSN3 (0.8 mL, 5.7 mmol) was added dropwise. The mixture was stirred at 100° C. for 2 hours. Water (10 mL) was added to the mixture. The mixture was filtered and the filter cake was washed with IPA (20 mL) to product (280 mg, yield 49%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09364481B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-fd495e09d6d4455f8d110e58619d178b
Source note	uspto-grants-2016_06