Ethylamine → HCID 18466607, compound
Reaction equation
[N+:1]([C:4]1[C:5](=O)[NH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].C1C=C[C:20]([N:23](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=[CH:19]C=1.C(N)C.C1COCC1>CN(C=O)C.O>[CH2:20]([NH:23][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[C:7]([C:10]([F:13])([F:12])[F:11])[N:6]=1)[CH3:19]Participants
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 3-nitro-6-(trifluoromethyl)-2(1H)-pyridinone (2.4 g, 11.5 mmol) in DMF (69 mL) was added sodium hydride (350 mg, 13.8 mmol). The reaction was stirred for 30 min at 45° C., cooled to room temperature and N-phenyltrifluromethanesulfonimide (4.9 g, 13.8 mmol) was added. After 1 h, a 2 M solution of ethylamine in THF (13 mL, 25 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was poured into water (100 mL) and extracted with EtOAc (3×). The combined organic layer was successively washed water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 9:1) to give the desired compound (1.1 g, 41% yield) as a yellow oil.
Workup
- temperaturecooled to room temperature
- waitAfter 1 h
- stirringThe reaction was stirred at room temperature overnight
- extractionextracted with EtOAc (3×)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography (hexane:EtOAc, 9:1)
Sources & evidence
- ORD record
- ord-c7f0614c755e478d96c844e241c18e90
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420359B1
Reaction notes
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