Potassium Carbonate → HCID 68209594, compound
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH:22]=[CH:21][N:20]=[N:19]1>CN1CCCC1=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([N:19]2[N:20]=[CH:21][CH:22]=[N:18]2)=[C:3]([C:9](=[O:11])[CH3:10])[CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a solution of 2′,5′-difluoroacetophenone (10.0 g, 64 mmol) in 1-methyl-2-pyrrolidinone (10 mL) was added potassium carbonate (8.84 g, 64 mmol) and 1H-1,2,3-triazole (6.64 g, 96 mmol). This mixture was heated to 140° C. for 3 hr, under an atmosphere of nitrogen. After this time, the reaction was cooled and then partitioned between ethyl acetate (300 mL) and aqueous ammonium chloride solution (1M, 100 mL). The organic phase was washed with water (3×200 mL) and then dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with ethyl acetate in heptane (10:90 by volume) to produce the title compound as a brown oil (4.6 g, 35%).
Workup
- temperatureAfter this time, the reaction was cooled
- custompartitioned between ethyl acetate (300 mL) and aqueous ammonium chloride solution (1M, 100 mL)
- washThe organic phase was washed with water (3×200 mL)
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by chromatography on silica gel eluting with ethyl acetate in heptane (10:90 by volume)
Sources & evidence
- ORD record
- ord-a94988ef766644ef9b662f2c3dd35fd7
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916593B2
Reaction notes
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