Water → 5-methoxy-4-(3-phenoxybenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

To a solution of 575 mg (5 mmol) of 5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one in 7 ml of dry acetonitrile was added 726 mg (5.25 mmol) of potassium carbonate was added. A solution of 1.32 g (5 mmol) of 3-phenoxybenzylbromide in 9 ml of dry acetonitrile was added dropwise thereto at 55° C. After the mixture was stirred at the same temperature for additional 5.5 hours, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. To the resultant solid residue (1.36 g) was added a mixture of equal amounts of tert-butyl methyl ether and n-hexane. The mixture was cooled and the deposited solid was washed, ice-cooled, collected by filtration, and dried to obtain a residue. The residue was recrystallized from tert-butyl methyl ether to obtain 0.27 g of 5-methoxy-4-(3-phenoxybenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one as white powder.

1. additionwas added
2. customat 55° C
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with water
5. customdried
6. concentrationconcentrated
7. additionTo the resultant solid residue (1.36 g) was added
8. additiona mixture of equal amounts of tert-butyl methyl ether and n-hexane
9. temperatureThe mixture was cooled
10. washthe deposited solid was washed
11. temperatureice-cooled
12. filtrationcollected by filtration
13. customdried
14. customto obtain a residue
15. customThe residue was recrystallized from tert-butyl methyl ether

ORD record

ord-b7412479d54548a6a3dd9558fe2b0817

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06489487B1