Hydrazine hydrate (1:1) → HCID 70563549, compound

Temperature

0 °C

In a 500-mL, 3N round-bottomed flask equipped with nitrogen inlet, and a rubber septum, (isobutyl carbonic) (Z)-3-(3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylic anhydride was cooled at 0° C. and added hydrazine hydrate (22.32 mL, 5.7 eq.). Reaction mixture was stirred at 0° C. for 1 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH-dichloromethane as mobile phase. SM Rf=0.6 and Product Rf=0.4. Reaction mixture was filtered through celite bed. Filtrate was poured into ice water (5000 mL) and extracted with EtOAc (3×500 mL). The combined organic layers were washed with brine solution (3×50 mL), dried over MgSO4, filtered, and concentrated by rotary evaporation (25° C., 20 mmHg) to afford 0.920 g of crude compound which was used for next step without further purification.

1. customIn a 500-mL, 3N round-bottomed flask equipped with nitrogen inlet
2. customReaction mixture
3. customReaction mixture
4. filtrationwas filtered through celite bed
5. additionFiltrate was poured into ice water (5000 mL)
6. extractionextracted with EtOAc (3×500 mL)
7. washThe combined organic layers were washed with brine solution (3×50 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated by rotary evaporation (25° C., 20 mmHg)

ORD record

ord-8254c2edc2b54e0baeede8948a0d5202

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303000B2