Sulfuric Acid → HCID 71542042, compound

Participants

Reaction Steps

N-(3,4-dichlorophenyl)-2-(2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetyl)hydrazinecarbothioamide (0.15 g, 0.341 mmol) and concentrated sulfuric acid (1 mL) were placed in a reaction beaker and the mixture was subjected to ultrasonic irradiation for 15 min. The reaction contents were poured into ice cold water. The precipitate was filtered and basified with 10% sodium bicarbonate (30 mL). Crude product was crystallized with ethanol/DMSO to afford 6-((5-(3,4-dichlorophenylamino)-1,3,4-thiadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (0.045 g, 31%) as an off white solid. 1H NMR 400 MHZ, DMSO-d6: δ 2.42 (dd, J=7.20, 8.20 Hz, 2H), 2.85 (t, J=7.60 Hz, 2H), 5.37 (s, 2H), 6.79 (d, J=8.80 Hz, 1H), 6.88 (dd, J=2.40, 8.60 Hz, 1H), 6.95 (d, J=2.00 Hz, 1H), 7.48 (dd, J=2.40, 8.80 Hz, 1H), 8.08 (d, J=2.80 Hz, 1H), 9.96 (s, 1H), 10.75 (s, 1H). LCMS: RT 1.97 min, LCMS (ES-API), m/z 423.0 (M+H).

Provenance & Evidence