Amitrole → HCID 67008740, compound

To a solution of 1H-1,2,4-triazol-5-amine (1.6 g) in acetic acid (30 mL) was added (2R,6S)-2,6-dimethyltetrahydro-4H-pyran-4-one (2.5 g) at room temperature, and the mixture was stirred for 30 min. After stirring, sodium triacetoxyborohydride (5.2 g) was added, and the mixture was stirred at room temperature for 20 hr. Acetic acid was evaporated and ethyl acetate and water were added to the residue. The mixture was neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in a small amount of ethyl acetate, and the mixture was crystallized from diisopropyl ether. The resulting solid was collected by filtration, washed with diisopropyl ether, and dried by heating under reduced pressure to give the title compound as a pale-yellow solid (1.6 g, 49%).

1. stirringAfter stirring
2. stirringthe mixture was stirred at room temperature for 20 hr
3. customAcetic acid was evaporated
4. additionethyl acetate and water were added to the residue
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with water and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated
9. dissolutionThe residue was dissolved in a small amount of ethyl acetate
10. customthe mixture was crystallized from diisopropyl ether
11. filtrationThe resulting solid was collected by filtration
12. washwashed with diisopropyl ether
13. customdried
14. temperatureby heating under reduced pressure

ORD record

ord-597caf5348ae442e8ad6c22644bf03d0

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115136B2