Water → B 115
Reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:10]=[C:9]([N+]([O-])=O)[CH:8]=[C:7](Cl)[C:5]=1N.F[C:16]1[C:23]([C:24]#N)=[C:22](F)[C:21](F)=C(F)C=1C#N.O.[CH3:30][N:31]([CH:33]=O)[CH3:32]>>[CH3:30][N:31]1[CH2:33][CH:16]=[C:23](/[CH:22]=[CH:21]/[C:4]2[C:5]3[C:7](=[CH:10][CH:4]=[CH:5][CH:7]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:24][CH2:32]1.[ClH:3]Participants
Procedure
3.12 g (0.078 mol) of sodium hydroxide was added to a solution of 8.07 g (0.039 mol) of 2,6-dichloro-4-nitroaniline in 60 mL of DMF, followed by addition of 7.80 g (0.039 mol) of 2,4,5,6-tetrafluoroisophthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:5, as an eluent) to give 8.08 g of compound B-115 as yellowish solid, m.p. 164-166° C.
Workup
- stirringthe mixture was stirred for 5 h
- additionafter addition at room temperature
- extractionextracted with ethyl acetate
- washthe organic phase was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:5
Sources & evidence
- ORD record
- ord-6d6989ff70144543869194681668b900
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937072B2
Reaction notes
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