Hydrazine hydrate (1:1) → HCID 70563549, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([O:22]C(=O)/C=C\N3C=NC(C4C=C(C(F)(F)F)C=C(OC)C=4)=N3)=O)[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.[NH2:45][NH2:46]>CCOC(C)=O.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([NH:45][NH2:46])=[O:22])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 50-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 (0.911 g, 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 50% EtOAc-hexane as mobile phase. SM Rf=0.6 and Product Rf=0.4. Reaction mixture was poured into ice water (50 mL) and extracted with EtOAc (3×50 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.
Workup
- customIn a 50-mL, 3N round-bottomed flask equipped with nitrogen inlet
- customReaction mixture
- customReaction mixture
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with brine solution (3×50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated by rotary evaporation (25° C., 20 mmHg)
Sources & evidence
- ORD record
- ord-af0c7e3b182649ab9d5a513f73c02f9c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303000B2
Reaction notes
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