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

HRID 55814Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:21]=[CH:20][C:16]([C:17](=[S:19])[NH2:18])=[CH:15][CH:14]=1)[CH:7]=[CH:6]2.[C:22](Cl)(=[O:26])C(Cl)=O.[Si]([N:32]=[N+]=[N-])(C)(C)C.O>ClCCCl.CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:21]=[CH:20][C:16]([C:17]3[S:19][NH:32][C:22](=[O:26])[N:18]=3)=[CH:15][CH:14]=1)[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 90 °C

Procedure

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%).

Workup

filtrationThe mixture was filtered

Sources & evidence

ORD record: ord-19c4ea5a67824c7ca1dab9e0753361c9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09433618B2

Reaction notes

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