Réaction #84092

ord-19c4ea5a67824c7ca1dab9e0753361c9

Équation de réaction

O
Water
C[Si](C)(C)N=[N+]=[N-]
TMSN3
COc1ccc2nc(-c3ccc(C(N)=S)cc3)ccc2c1
4-(6-methoxyquinolin-2-yl)benzothioamide
O=C(Cl)C(=O)Cl
oxalylchloride
COc1ccc2nc(-c3ccc(-c4nc(=O)[nH]s4)cc3)ccc2c1
product
Rendement 78.0%
COc1ccc2nc(-c3ccc(-c4nc(=O)[nH]s4)cc3)ccc2c1
5-(4-(6-methoxyquinolin-2-yl)phenyl)-1,2,4-thiadiazol-3(2H)-one
Rendement 78.0%

Solvants

Conditions de réaction

Température
90°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe mixture was filtered

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09433618B2uspto-grants-2016_09