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ChemicalBook CAS DataBase List 2,4-DIHYDRO-4-[(4-(4-HYDROXYPHENYL)-1-PIPERAZINYL)PHENYL]-2-(1-METHYLPROPYL)-3H-1,2,4-TRIAZOLE-3-ONE
106461-41-0

2,4-DIHYDRO-4-[(4-(4-HYDROXYPHENYL)-1-PIPERAZINYL)PHENYL]-2-(1-METHYLPROPYL)-3H-1,2,4-TRIAZOLE-3-ONE synthesis

10synthesis methods
-

Yield: 98%

Reaction Conditions:

with hydrogen bromide in water at 120;Heating / reflux;

Steps:

1.A
Triazolone 9 (0.50 g, 1.2 mmol) was added to HBr (48%, 5 mL). The reaction mixture was heated to 1200C and refluxed overnight. The reaction mixture was cooled to room temperature, while a pink solid precipitated. The solid was collected by filtration, dissolved in methanol-water (1 : 1, 40 mL), saturated aqueous NaHCO3 (20 mL) was added, and extracted with chloroform (3 x 20 mL). The organic layer was washed with brine and dried over MgSO4. The solvent was removed to obtain phenol 10 (0.48 g , 98% yield).MP: 76-78 0C.1H NMR (400 MHz, CDCl3): δ 7.63 (s, IH), 7.39 (d, J= 8.8 Hz, 2H), 7.00 (d, J= 9.2 Hz, 2H), 6.85 (d, J= 8.8 Hz, 2H), 6.72 (d, J= 8.8 Hz, 2H), 5.74 (br s, IH), 4.26-4.35 (m, IH), 3.32-3.40 (m, 4H), 3.18-3.25 (m, 4H), 1.65-1.91 (m, 2H), 1.41 (d, J= 6.8 Hz, 3H), 0.91 (t, J= 7.2 Hz, 3H).MALDI-MS: 394.3 (M+H*), 416.3 (M+Naí).

References:

THE JOHNS HOPKINS UNIVERSITY WO2008/124132, 2008, A1 Location in patent:Page/Page column 49-50

2,4-DIHYDRO-4-[(4-(4-HYDROXYPHENYL)-1-PIPERAZINYL)PHENYL]-2-(1-METHYLPROPYL)-3H-1,2,4-TRIAZOLE-3-ONE Related Search: